Should I refi a rental property to reduce income tax from positive cash flow and use the equity pulled out to fund an annuity?
"You need to do a bit more research and as @littleadv often wisely advises, consult a professional, in this case a tax layer or CPA. You are not allowed to just pull money out of a property and write off the interest.  From Deducting Mortgage Interest FAQs If you own rental property and borrow against it to buy a home, the   interest does not qualify as mortgage interest because the loan is not   secured by the home itself. Interest paid on that loan can't be   deducted as a rental expense either, because the funds were not used   for the rental property. The interest expense is actually considered   personal interest, which is no longer deductible. This is not exactly your situation of course, but it illustrates the restriction that will apply to you.  Elsewhere in the article, it references how, if used for a business, the interest deduction still will not apply to the rental, but to the business via schedule C.  In your case, it's worse, you can never deduct interest used to fund a tax free bond, or to invest in such a tax favored product.  Putting the facts aside, I often use the line ""don't let the tax tail wag the investing dog."" Borrowing in order to reduce taxes is rarely a wise move. If you look at the interest on the 90K vs 290K, you'll see you are paying, in effect, 5.12% on the extra 200K, due the higher rate on the entire sum. Elsewhere on this board, there are members who would say that given the choice to invest or pay off a 4% mortgage, paying it off is guaranteed, and the wiser thing to do. I think there's a fine line and might not be so quick to pay that loan off, an after-tax 3% cost of borrowing is barely higher than inflation. But to borrow at over 5% to invest in an annuity product whose terms you didn't disclose, does seem right to me. Borrow to invest in the next property? That's another story."
It is great that you came up with a plan to own a rental home, free and clear, and also move up in home.  It is also really good of you to recognize that curtailing spending has a profound effect on your net worth, many people fail to acknowledge that factoid and prefer to instead blame things outside their control.  Good work there.  Here are some items of your plan that I have comments on. 11mo by aggressively curtailing elective spending How does your spouse feel about this?  They have to be on board, but it is such a short time frame this is very doable. cashing out all corporate stock, This will probably trigger capital gains.  You have to be prepared to pay the tax man, but this is a good source of cash for your plan.  You also have to have an additional amount that will likely be due next April 15th. redirecting all contributions to my current non-matched R401(k) This is fine as well because of the short time frame. withdrawing the principal from a Roth IRA This I kind of hate.  We are so limited in money that we can put into tax favored plans, that taking money out bothers me.  Also it is that much more difficult to save in a ROTH because of the sting of taxes.  I would not do this, but would favor instead to take a few extra months to make your plan happen. buy home #2 How are you going to have a down payment for home #2?  Is your intention to pay off home and save a while, then purchase home #2?  I would do anything to avoid PMI.   Besides I would take some time to live in a paid for house. Overall I would grade your plan a B.  If take a bit longer, and remove the withdrawing from the ROTH, it then becomes an A-.  With a good explanation of how you come up with the down payment for house 2, you could easily move to an A+. Purchase capital asset (deductible expense). Sell capital asset next year, then use the proceeds of the sale to pay your employees.  Unless you buy in a quickly gentrifying area you'll have a fair amount of unrecoverable expenses like closing costs, repairs, etc that you won't make up with an increase in property value. Plus property taxes, utilities, etc. And who knows how quickly you can sell the place, might end up with a bloated useless asset and no money to pay employees. And in an audit an asset purchased with no actual use to the business will get disallowed.  Either retain the earnings and take the tax hit, or make a deal with your employees to pre pay them their next year's salary. Of course if you fire someone or they quit good luck getting the overpaid portion back. If your mortgage interest is tax-deductible, it's generally a bad idea to pay down the principal on the mortgage because you'd be losing the tax deduction. You could instead invest it in a tax-free municipal bond fund, especially if you're in a high tax bracket (including state and local marginal tax rates). For example, if you have a 5% rate mortgage on your home, you could invest in a 3.5% municipal bond and still come out ahead when you apply the tax deduction to your income at a 44% (33% federal + 7% state + 4% city in NYC) marginal tax rate. Wow, hard to believe not a single answer mentioned investing in one of the best asset classes for tax purposes...real estate.  Now, I'm not advising you to rush out and buy an investment property.  But rather than just dumping your money into mutual funds...over which you have almost 0 control...buy some books on real estate investing.  There are plenty of areas to get into, rehabs, single family housing rentals, multifamily, apartments, mobile home parks...and even some of those can have their own specialties.  Learn now! And yes, you do have some control over real estate...you control where you buy, so you pick your local market...you can always force appreciation by rehabbing...if you rent, you approve your renters.  Compared to a mutual fund run by someone you'll never meet, buying stocks in companies you've likely never even heard of...you have far more control. No matter what area of investing you decide to go into, there is a learning curve...or you will pay a penalty.  Go slow, but move forward. Also, all the advice on using your employer's matching (if available) for 401k should be the easiest first step.  How do you turn down free money?  Besides, the bottom line on your paycheck may not change as much as you think it might...and when weighed against what you get in return...well worth the time to get it setup and active. Definitely don't borrow from your 401K.  If you quit or get laid off, you have to repay the whole amount back immediately, plus you are borrowing from your opportunity cost.  The stock market should be good at least through the end of this year.   As one of the commentators already stated, have you calculated your net savings by reducing the interest rate?  You will be paying closing costs and not all of these are deductible (only the points are).  When calculating the savings, you have to ask yourself how long you will be hanging on the property?  Are you likely to be long term landlords, or do you have any ideas on selling in the near future?   You can reduce the cost and principal by throwing the equivalent of one to two extra mortgage payments a year to get the repayment period down significantly (by years).  In this way, you are not married to a higher payment (as you would be if you refinanced to a 15 year term).   I would tend to go with a) eat the appraisal cost, not refinance, and b) throw extra money towards principal to get the term of the loan to be reduced. In general you do not want to show a taxable gain on rental properties if you can avoid it.  One of the more beneficial advantages of owning cash flowing rental properties, is that the income is tax deferred because of the depreciation.  I say deferred, because depreciation affects the cost basis of your property.   Also since you are considering financing, it sounds like you don't need the cash flow currently.  You usually can get better returns by financing and buying more rental properties, especially with investment mortgages at historical lows (Win via inflation over time) "http://www.investopedia.com/articles/mortgages-real-estate/08/tax-deductible-mortgage-canada.asp  &gt; This strategy is not for everyone. Borrowing against your home is psychologically difficult, and if the investments don't yield expected returns, this strategy could yield negative results. By re-borrowing the equity in your home, you are also removing your ""cushion"" of safety if the real estate (or investment) markets take a turn for the worse. By creating an income-producing portfolio in an unregistered account, there can also be additional tax consequences - so always consult with a professional financial advisor to determine whether this strategy is for you, and if it is, have it tailor-made to you and your family's personal financial situation." Basically there are 2 ways you can make money from an investment, through income (eg: rent or dividends) and through the price of the investment going up (capital growth or gains). Most people associate negative gearing with investment properties but it can be done with shares and other investments where you borrow money to buy the investment and it produces an income of some sort. If the investment does not produce an income then you cannot negative gear it. Using a property as an example (in Australia), if all your expenses each month (loan interest payments, council and water rates, insurance and/or strata, advertising and management fees, depreciation, and maintenance expense) are greater than your income (rent), then you are negative gearing the investment property. This is a monthly loss on your investment which can be used to offset and reduce the amount of tax you pay during the year. So most people negative gearing an investment property will get a nice sum back when they do their tax returns. The problem with negative gearing is that you have to lose money in order to save some tax. So as an example, if you are on a marginal tax rate of 30%, for every $1 you lose from the investment property you will save 30c in tax. If your marginal tax rate is 45% then will save 45c in tax for every $1 lost on the investment property. Thus negative gearing becomes more tax effective the higher your income (and tax bracket). But you are still losing money overall. The problem is that most novice investors buy an investment property for the main purpose of reducing their taxes. This can be dangerous because the main reason to buy any investment should be that you consider it to be a good investment, not to save you tax. Because if the investment is not a good one, then you will not only lose money on the income side but also on the capital side. Negative gearing should be looked at as a bonus or additional benefit when chosing a good investment to buy, not as the reason to buy the investment. I would not claim to be a personal expert in rental property. I do have friends and family and acquaintances who run rental units for additional income and/or make a full time living at the rental business.  As JoeTaxpayer points out, rentals are a cash-eating business. You need to have enough liquid funds to endure uncertainty with maintenance and vacancy costs. Often a leveraged rental will show high ROI or CAGR, but that must be balanced by your overall risk and liquidity position. I have been told that a good rule-of-thumb is to buy in cash with a target ROI of 10%. Of course, YMMV and might not be realistic for your market. It may require you to do some serious bargain hunting, which seems reasonable based on the stagnant market you described. Some examples: The main point here is assessing the risk associated with financing real estate. The ROI (or CAGR) of a financed property looks great, but consider the Net Income. A few expensive maintenance events or vacancies will quickly get you to a negative cash flow. Multiply this by a few rentals and your risk exposure is multiplied too!  Note that i did not factor in appreciation based on OP information. Cash Purchase with some very rough estimates based on OP example Net Income = (RENT - TAX - MAINT) = $17200 per year Finance Purchase rough estimate with 20% down Net Income = (RENT - MORT - TAX - MAINT) = $7500 per year You're not crazy, but the banks are. Here's the problem: You're taking 100% LTV on property A - you won't be able to get a second mortgage for more than 80% total (including the current mortgage) LTV. That's actually something I just recently learned from my own experience. If the market is bad, the banks might even lower the LTV limit further. So essentially, at least 20% of your equity in A will remain on the paper. Banks don't like seeing the down-payment coming from anywhere other than your savings. Putting the downpayment from loan proceeds, even if not secured by the property which you're refinancing, will probably scare banks off. How to solve this? Suggest to deal with it as a business, putting both properties under a company/LLC, if possible. It might be hard to change the titles while you have loans on your properties, but even without it - deal with it as if it is a business. Approach your bank for a business loan - either secured by A or unsecured, and another investment loan for B. Describe your strategy to the banker (preferably a small community bank in the area where the properties are), and how you're going to fund the properties. You won't get rates as low as you have on A (3.25% on investment loan? Not a chance, that one is a keeper), but you might be able to get rid of the balloon/variable APR problem. You can't pay your bills with equity in your house. Assuming you paid off the mortgage, where would the money come from that you plan to live off of? If that is your whole retirement savings I'd say do neither. Maybe an annuity (not variable) for SOME of the money, keep the rest invested in conservative investments some of it in cash for emergencies. That is a decision you need to make, but some of the pros and cons you could consider to help your decision making include: Pros: If bought at the right time in the property cycle and in a good growth area, it can help you grow your net worth much quicker than having money in the bank earning near zero interest. You would be replacing rent payments with mortgage payments and if your mortage payments are less than your current rent you will have additional money to pay for any expenses on the property and have a similar cashflow as you do now. You will be able to deduct your interest payments on the mortgage against your income if you are in the USA, thus reducing the tax you pay. You will have the security of your own house and not have to worry about moving if the landlord wants you out after your lease expires. Cons: If bought in a bad area and at the top of the property cycle you may never make any capital gains on the property and in fact may lose money on it long term. If the mortgage payments are more than your current rent you may be paying more especially at the start of your mortgage. If you buy a house you are generally stuck in one spot, it will be harder to move to different areas or states as it can cost a lot of money and time to sell and buy elsewhere, if renting you can generally just give notice and find a new place to rent. Property maintenance costs and taxes could be a drain on your finances, especially if the mortgage repayments are more than your current rent. If your mortgage payments and property expenses are way more than your current rent, it may reduce what you could be investing in other areas to help increase your net worth. To start, I hope you are aware that the properties' basis gets stepped up to market value on inheritance.  The new basis is the start for the depreciation that must be applied each year after being placed in service as rental units. This is not optional. Upon selling the units, depreciation is recaptured whether it's taken each year or not. There is no rule of thumb for such matters. Some owners would simply collect the rent, keep a reserve for expenses or empty units, and pocket the difference. Others would refinance to take cash out and leverage to buy more property. The banker is not your friend, by the way. He is a salesman looking to get his cut. The market has had a good recent run, doubling from its lows. Right now, I'm not rushing to prepay my 3.5% mortgage sooner than it's due, nor am I looking to pull out $500K to throw into the market.  Your proposal may very well work if the market sees a return higher than the mortgage rate. On the flip side I'm compelled to ask - if the market drops 40% right after you buy in, will you lose sleep?  And a fellow poster (@littleadv) is whispering to me - ask a pro if the tax on a rental mortgage is still deductible when used for other purposes, e.g. a stock purchase unrelated to the properties.   Last, there are those who suggest that if you want to keep investing in real estate, leverage is fine as long as the numbers work. From the scenario you described, you plan to leverage into an already pretty high (in terms of PE10) and simply magnifying your risk. Your question is best asked of a tax expert, not random people on the internet. Such an expert will help you ask the right questions.  For example you did not point out the country or state in which you live.  That matters.   First point is that you will not pay tax on 60K, its expensive to transact real estate, so your net proceeds will be closer to 40K.  Also you can probably the deduct the costs of improvements. You implied that you really like this rental property.  If that is the case, why would you sell...ever?  This home could be a central part of your financial independence plan.  So keep it until you die.  IIRC when it passes to your heirs, a new cost basis is formed thereby not passing the tax burden onto them. (Assuming the property is located in the US.) "First, let's look at the tax brackets for single taxpayers in 2016: The cutoff between the 25% and 28% tax bracket is $91,150.  You said that your gross is $87,780.  This will be reduced by deductions and exemptions (at least $10,350).  Your rental income will increase your income, but it is offset in part by your rental business expenses. For this year, you will almost certainly be in the 25% bracket, whether or not you receive your backpay this year.  Next year, if you receive your backpay then and your salary is $11k higher, I'm guessing you'll be close to the edge. It is important to remember that the tax brackets are marginal.  This means that when you move up to the next tax bracket, it is only the amount of income that puts you over the top that is taxed at the higher rate.  (You can see this in the chart above.)  So if, for example, your taxable income ends up being $91,160, you'll be in the 28% tax bracket, but only $10 of your income will be taxed at 28%.  The rest will be taxed at 25% or lower.  As a result, this probably isn't worth worrying about too much. A bit more explanation, requested by the OP: Here is how to understand the numbers in the tax bracket chart.  Let's take a look at the second line, $9,276-$37,650.  The tax rate is explained as ""$927.50 plus 15% of the amount over $9,275.""  The first $9,275 of your taxable income is taxed at a 10% rate.  So if your total taxable income falls between $9,276 and $37,650, the first $9,275 is taxed at 10% (a tax of $927.50) and the amount over $9,275 is taxed at 15%.  On each line of the chart, the amount of tax from all the previous brackets is carried down, so you don't have to calculate it. When I said that you have at least $10,350 in deductions and exemptions, I got that number from the standard deduction and the personal exemption amount.  For 2016, the standard deduction for single taxpayers is $6,300.  (If you itemize your deductions, you might be able to deduct more.)  Personal exemptions for 2016 are at $4,050 per person.  That means you get to reduce your taxable income by $4,050 for each person in your household.  Since you are single with no dependents, your standard deduction plus the personal exemption for yourself will result in a reduction of at least $10,350 on your taxable income."