Would parking at a parking lot near or in my residence prevent me from paying for it with my transit FSA?
"No, it doesn't look like you can use the employee benefit to pay for parking near your home. The definition for ""qualified parking"" is in the Internal Revenue Code Section 132 (""Certain Fringe Benefits"") (f) (5) (c): (C) Qualified parking The term “qualified parking” means parking provided to an employee on or near the business premises of the employer or on or near a location from which the employee commutes to work by transportation described in subparagraph (A), in a commuter highway vehicle, or by carpool. Such term shall not include any parking on or near property used by the employee for residential purposes.  Parking near your home is explicitly excluded. Your employer's human resources department can probably provide information on the details of where you can park and get reimbursement."
You pay in advance - and there are no refunds.  I bought a van last fall, and paid no property tax on it, because it was already covered through whatever end date the registration had.  I will pay taxes on it this year, though (presuming I still have it). Well you've got to think about the process, but first make sure the thing you want to pay for is actually a qualified dependent care expense.  Here is a list of eligible expenses from a national FSA administrator. This process will tie up your money for some amount of time.  Your deduction will come out like clockwork.  But there is a time-delay of potentially months between your deduction and receipt of a reimbursement. Dependent care plans are money-in money-out.  You can only file a reimbursement on funds that have actually been contributed, which is different than a medical FSA.  Additionally, you can only file a claim on expenses that have actually been incurred.  Dependent care FSA elections can be changed through the year on an as needed basis.  This would add an administrivia burden to the person running your payroll, and if there is a payroll vendor in place, likely an actual cost.  The administrator in this situation would likely be the company.  In the formalities of employee benefits there must always be a named administrator. If your employer currently offers no benefits you should press healthcare first.  Paying healthcare premiums pretax would likely save you more money and be less administration than this.  Additionally, if your employer is paying for or reimbursing you for your individual health insurance that's currently illegal under the ACA. Two companies I worked for in the DC area also did WageWorks. The commuting money could be used for the Subway, Bus, and commuter rail. A separate pot of money was used for parking.  We had to estimate the amount of money that would be used the next month. We had to decide by mid-June how much we would spend in July. The money was automatically added to the metro fare card on the first business day of the month. When I first started they put the money on a special debit/credit card that could only be used at commuter system. It would be rejected at the department store. If parking couldn't be paid using a special card, there was a way to claim the money with or without receipts. If the company, like the US Government does for their employees, paid the commuting expenses any excess funds at the end of the month were pulled back from the card. They were just starting to do this in 2012 for employee pre-tax funds. They were supposed to add it to your next paycheck any excess at the end of the month. There was also a way to use post tax funds from your paycheck so that all your commuting expenses could be on one card. Of course any post-tax funds would be left on the card. There was no real way for them to audit this because the system would never know if you were going to work or going to the dentist. I ended up using two cards, one for work and one for non-work usage. There is no special activity type (or provider) for this situation. Depending on the car rental agency, it is either a normal charge, and they later return the charge as necessary; or it is a normal authorization (like in a restaurant) that does never get confirmed (so it falls off the credit card after about three days). I don't see how allowing usage of your vehicle is less support than giving money to buy their own vehicle. If that's the only vehicle your mother has - then you're supporting her. Quantifying that support may be difficult though, but if you are providing her all of her needs - it doesn't matter. If she does have income of her own, I do not think that you can put the actual amount you're paying as part of the calculation towards the 50% rule since she would otherwise have bought a much cheaper car. But if you pass the 50% threshold even without the car payments - then you're fine either way. "As you're saving up for an expenditure instead of investing for the long run, I would stay away from any sort of ""parking facility"" where you run the risk of not having the principal protected. The riskier investments that would potentially generate a bigger return also carry a bigger downside, ie you might not be able to get the money back that you put in. I'd shop around for a CD or a MMA/regular savings account with a half-decent interest rate. And yes, I'm aware that the return you might get is probably still less than inflation." I believe moving reimbursement has to be counted as income no matter when you get it. I'd just put it under miscellaneous income with an explanation. It is the people who you bought the ticket from. Blocking is frequently done by hotels, gas stations, or rental car companies. Also, for anything where the credit card might be used to cover any damages or charges you might incur later as part of the transaction. In essence, they are reserving part of your credit limit, ostensibly to cover charges they reasonably expect you might incur. For example, when you start pumping gas using a credit card they may block out $100 to make sure you don't pump a full tank and your credit card is declined because you ran over your limit at $3.  In general, the blocks clear fairly quickly after you settle up with the company on your final bill. You can also ask the company to clear the block, but I don't think they are required to by law in any specific time period. It may be up to their (and your) agreement with the credit card company. Normally it isn't an issue and you don't even notice this going on behind the scenes, but if you keep your credit card near its limit, or use a debit card it can lead to nasty surprises (e.g. they can make you overdraw your account). One more reason not to use debit cards. More information is available here on the Federal Trade Commission's website. FSA is a convenience to allow you to pay day care expenses with pre-tax money.   It sounds like neither you nor your wife are eligible through an employer, so you can't use one. If you do not use FSA, then at tax time you can deduct the cost of day care from your gross income.  In the end the effect is the same.  Just keep track of your expenses. You cannot deduct expenses directly.  However, your employer may participate in programs to allow you to make a pretax deduction capped at $255 per month to pay for certain commuting expenses.  For personal car commuters the main category is to pay for parking.   IRS guidelines Qualified Transportation Benefits This exclusion applies to the following benefits. A ride in a commuter highway vehicle between the employee's home and   work place. A transit pass. Qualified parking. Qualified bicycle commuting reimbursement. You may provide an employee with any one or more of the first three   benefits at the same time. However, the exclusion for qualified   bicycle commuting reimbursement isn't available in any month the   employee receives any of the other qualified transportation benefits. "One additional penalty is you will be put on the CAIVRS (""cavers"") for your default on the FHA mortgage which will preclude you from FHA financing in the future. When purchasing the multifamily unit it is an FHA requirement that you occupy one of the units.   Lastly, I would advise against FHA due to elevated costs.  Conventional options have 95% financing options, and don't have mortgage insurance that lasts forever, like FHA does." Here in the DC area, we have MetroAccess, which is subsidized by WMATA (the organization that runs DC's Metro and Metrobus system) and offers rides to disabled folks almost like a personal taxi service.  If New York doesn't have something like that now, if they're willing to pay for it, they could implement a public option to address any possible failure in the private market if companies like Uber are unable to do it. It may seem very simple on its face but you don't know the merchant's agreement.  You don't know who is providing the processing equipment.  You don't know a lot of things.  You know that Visa, Mastercard, Discover, Amex and others have network requirements and agreements.  You know that laws have been changed to allow merchant surcharges (previously it was contracts that prohibited surcharges, not laws).   That gas station, or that pizza parlor, or any other merchant doesn't have a direct relationship with Visa or Mastercard; it has an agreement with a bank or other processing entity.  The issue here, is whom do you even call?  And what would you gain?  Find out what bank is contracted for that particular equipment and file a complaint that the merchant charged you $0.35?  Maybe the merchant agreement allows surcharges up to state and local maximums?  You don't know the terms of their agreement.  Calling around to figure out what parties are involved to understand the terms of their agreement is a waste of time, like you said you can just go across the street if it's so offensive to you.  Or just carry a little cash.   If that's not the answer you're looking for, here's one for you: There is no practical recourse. Given that a lot of rental car places tend to be co-located these days, I've just started making multiple reservations. There's generally no penalty for not picking up the car and if one flakes out, you still have a reservation elsewhere. "It depends on the rules in the specific places you stay.  Specific places being countries or states.   Some states may consider pension payments to be taxable income, others may not.  Some may consider presence for X days to constitute residency, X days may be 60 days in a calendar year whether or not those days are continuous.   It doesn't matter so much where your mailbox or mail handling service is located, it matters: You may owe taxes in more than one place.  Some states will allow you to offset other states' taxes against theirs.  Some states in the US are really harsh on income taxes.  It's my understanding that if you own real estate in New York, all of your income, no matter the source, is taxable income in New York whether or not you were ever in the state that year. Ultimately, you can't just put up your hand and say, ""that's my tax domicile so I'm exempt from all your taxes.""  There is no umbrella US regulation on this topic, the states determine who they consider to be residents and how those residents are to be taxed. While it's possible you may be considered a resident of multiple states and owe income taxes in multiple states, it's equally possible that you won't meet the residency criteria for any state regardless of whether or not that state has an income tax.  The issue you face, as addressed in @Jay's answer, Oklahoma will consider you a resident of OK until you have established residency somewhere else."