I Couldn’t Afford a Home — Then I Ignored ‘Boomer’ Advice and Bought 3

For most of my adult life, I assumed I’d never be able to own a home. I’ve lived in big cities since graduating college, and as any New Yorker can attest, even a 300-square-foot “starter home” can easily cost a million dollars. I resigned myself to the millennial stereotype, endlessly scrolling Zillow like it’s social media while consoling myself with avocado toast and $8 lattes.

But then I discovered a strategy that changed everything.

I realized I didn’t need to buy where I lived. Instead, I could continue renting my primary home (ignoring the collective head-shake from boomers) and buy a vacation home somewhere more affordable.

Related: Why Real Estate Should Be a Key Part of Your Wealth-Building Strategy in 2025 and Beyond

This didn’t begin as a master plan to build generational wealth or create financial freedom (though those did come as a bonus). It started from a simple desire to have a place to call my own, a place to make memories with family and friends without the city-sized limitations I’d grown used to. My intentions were modest: I hoped to offset some of my costs by renting it out on Airbnb or Vrbo when I wasn’t there. But quickly, I realized I was onto something much bigger. Not only did short-term rental income cover my annual costs — it turned a profit. Within a year, I bought a second property. Twelve months later, a third.

Here’s the practical, tactical strategy that made it possible — and how you can use it to afford a home, even in this economy.

Rent your primary home, buy your ‘second home’ first

A recent Bankrate study showed that renting is now more affordable than buying in all 50 of the largest U.S. metros. In my case, purchasing a comparable apartment in my own neighborhood would have doubled my monthly cost — not to mention, added an out-of-reach down payment.

If, like me, you’ve reached the disappointing conclusion that you can’t afford to buy a home in the city where you live, the obvious “solution” is to either downsize or move somewhere else. But what if you can’t? Or you simply don’t want to?

According to RedFin, the median sold price in Manhattan was $1.3 million. Instead, I bought a home in Warren County, where the average was a much more reasonable $336,000.

Related: Why Buying a ‘Second Home’ First is the New Way to Build Wealth — and Enjoy Free Vacations

Check that renting your future vacation home is legal

For this approach to work, you need to be able to rent your vacation home when you’re not using it. So before you start calling realtors, check that short-term rentals are allowed in your desired destination. Many towns limit the number of nights you can rent, require registration, have zoning restrictions or outright bans. Knowing the rules up front can save you from major headaches later.

You can usually find the most up-to-date information on the town or county’s website. And when in doubt, take the old-school approach: pick up the phone and call their office directly.

Determine what your vacation home could earn

If your goal is for the home to cover its costs, you’ll need to estimate its earning potential. Several tools can help—AirDNA, PriceLabs Revenue Estimator Pro, and BNBCalc all provide property-specific income projections.

I’d also suggest reaching out to property management companies, both local ones in your area as well as national chains like Vacasa or Evolve. They’ll provide their own estimates (in hopes of winning your business).

Treat every projection as a guide, not gospel. I’m a worst-case-scenario planner myself, so I always run my numbers using the lowest estimate. I aim to have all of my expenses covered at the low end, but use the higher estimates as my stretch goal, giving me the confidence to move forward without overextending myself.

Ignore fear mongering headlines about interest rates and home prices

It feels like every day brings another alarmist headline about rising interest rates. Or when they drop, then rising home prices. Trying to “time the market” feels like trying to get in on a game of double-dutch.

But a vacation home (that you’ll use as a short-term rental) can be less sensitive to these fluctuations. Hear me out: if your projected rental income covers your costs at today’s purchase price and interest rate, there’s only upside should things improve. If interest rates fall, you can refinance and watch that change directly increase your profits.

And remember, lower interest rates often drive up home prices and create bidding wars. But since you’ll already own your property, you’ll be free to sit back and watch the chaos unfold from the sidelines.

When done right, your vacation home can work like a 401(k)

Buying my “second home” first felt radical at the time. I lost track of how many well-meaning relatives asked why I was still “throwing money away on rent”. But the numbers don’t lie.

For me, it turned out to be a breakthrough investment strategy, a way to make homeownership possible, even in today’s economy. Like a retirement account, the house offers long-term financial upside — growing in value, building equity and even providing income — but with two key differences. First, my mortgage is paid by short-term rental income, not by my own contributions. And second, when it’s not booked, I get to enjoy my vacation home now, not someday in the future.

It grows my wealth, offsets my taxable income and best of all? It gives me a place to vacation for free. What 401(k) can do that!?

For most of my adult life, I assumed I’d never be able to own a home. I’ve lived in big cities since graduating college, and as any New Yorker can attest, even a 300-square-foot “starter home” can easily cost a million dollars. I resigned myself to the millennial stereotype, endlessly scrolling Zillow like it’s social media while consoling myself with avocado toast and $8 lattes.

But then I discovered a strategy that changed everything.