Once again, I’d managed to flip my apartment and make a considerable profit. We now had a sizable sum of money to put down on our next home, but the astronomical asking prices in our preferred Brooklyn neighborhoods meant we’d be looking at a high monthly nut between mortgage and maintenance. Every time I crunched the numbers, it seemed like it didn’t make sense to make a purchase. We fretted about what to do, and my gut said we shouldn't buy. So, we didn’t. Instead, we found a good deal on a two-year rental. We decided to watch the market and bide our time.

While renting the first year, we drove out to East Hampton over the holidays for a night in a hotel as a pre-Christmas treat. Driving around in the cold that weekend, my husband wondered how much a waterfront listing might cost. So I opened my Trulia app and looked. We laughed at the high price tag, and as we drove, I watched the app's map and called out the asking prices for the homes we passed with "For Sale" signs. As we made our way west, I saw a listing pop up for $310,000 just north of the highway. Surprised and curious, I asked my husband to hook a right and drive towards the bargain listing. A half a mile later, we pulled into the driveway of a very small, but very real house. With my phone in hand, we looked at the interior photos while parked outside. It seemed unbelievable that here was an honest-to-goodness house that cost less than a studio apartment in our neighborhood. And that house was situated in one of the most luxurious resort towns in America!

As we drove back to Brooklyn that night, we did a lot of “what if” talk. What if we bought a house in the Hamptons? Still freelancers, we imagined living there half the week and spending the other half in the city. We knew the rental market out there was strong enough that we could surely rent the house to offset the cost of a mortgage. We imagined fixing something up and flipping it. We imagined not feeling so bad about cramped quarters back in the city if we had a weekend escape.

Reader, I dreamed of days at the beach.

At my computer that night, I ran a multiple-listings service search and was surprised once again to see that there were several houses for $300,000 in the area. I ran numbers through an online mortgage calculator and was cautiously optimistic that we could actually make this scheme work.

Over the next two months, we saw every house in the $300,000 range in the area — most of them were too dilapidated for us to consider. We expanded our budget and looked at everything under $400,000. I researched rental rates to guesstimate how much we could anticipate in rental income. I even made a complex spreadsheet that helped me figure out what we could really afford. Finally, with a bit of trepidation, we made an offer on a house for $399,000, which was accepted.

The house needed work, but I was hopeful we could be renting it within a year. I figured, with our profits from the last sale, we had enough for the down payment, renovations, and a little more left over for a future purchase back in the city. For the first time in my real-estate-buying history, my parents were not convinced I’d made the right choice. They believed that I’d underestimated how much the work would cost and overestimated how much I could rent the house for. Fortunately, they were right on only the first count. Bids for painting were so high that we did it ourselves (it took 10 months of painting nearly every weekend). We contracted out the bathroom renovations, which were a significant investment but unavoidable. By the second year, we had the house rented for the majority of the summer — my plan had worked.