The Ups and Downs of Living in School Housing
A Financial Chat for Educators
For over two decades, I have helped independent school administrators and teachers prepare for life after school with financial confidence. This article helps consolidate various alternative savings strategies for those currently living in school housing.
Let’s be honest—living in school housing has its perks. The lawn? Always neat. Grounds? Beautifully kept. Instant campus community? Often built-in. And if you're at a boarding school, those shared meals in the dining hall? Free and plentiful.
But here's the thing: while the convenience is real, it’s easy to overlook the long-term financial tradeoffs—especially when it comes to homeownership and building equity. This isn’t a piece about the professional duties that come with housing perks. It’s about figuring out how to make smart financial moves when your name isn’t on a deed.
There is no “one size fits all” solution here—just options to consider, and the one that fits you best.
💸Stick With the Basics—and Spend the Rest?
A lot of educators are ticking the right boxes—taking advantage of school retirement matches, choosing HSA-friendly health plans, and feeling pretty covered.
But here’s a question worth asking: are you saving the extra cash that others are putting toward a mortgage? Or are you using it for travel, dining out, and lifestyle upgrades?
If it’s the latter, no shame—but be careful. Unlike the 1970s, schools today aren't likely to offer a financial safety net for faculty who didn’t save enough along the way.
🏡Buy a Second Home
Some educators buy a vacation home to enjoy on school breaks—quiet towns, beach spots, mountain retreats. Think Cape Cod, Vermont, the Poconos. It’s a way to build equity and create a family legacy.
Sounds great, right? Just keep in mind—if you ever take a job without school housing, will you be able to swing two mortgages? That second home could quickly become a financial burden.
Also consider: Is this a place where you’d want to live full time? A snowy mountain town sounds dreamy…until the isolation sets in during long winters.
🏘️Invest in a Rental Property
Buying a rental can be a smart way to build long-term wealth. You pay down the mortgage, the property may appreciate, and you gain some portfolio diversity as well as personal diversity from your day-to-day school life.
Start early, and it could give you a solid financial boost by retirement. And if it’s in a location you might retire to? Even better—you're hedging against future real estate spikes.
Downside? It’s work. Managing a rental means dealing with turnover, repairs, and all the costs that come with maintaining a property. Not quite totally passive income.
💵Save Like You’re Paying a Mortgage
This one’s simple in theory, but tough in practice. Take the amount you’d be paying for a mortgage and stash it away—maybe in your 403(b), 401(k), or even a Roth account.
If you’re saving for a future down payment, a Roth might be the more flexible path tax-wise. Just be cautious—early withdrawals can trigger penalties or higher taxes depending on the account you save to.
To give you a sense of scale: if you're aiming for a $750,000 home 30 years from now, saving the max to a Roth ($23,500/year in 2025) and investing smartly could get you there with room to spare.
It takes discipline, though. That money is easy to spend if you’re not watching closely—and FOMO (Fear Of Missing Out) is real when your friends are hosting housewarming parties and you're still in campus quarters.
🎯Final Thoughts
None of these strategies is “right” or “wrong.” They all have potential, depending on your goals, lifestyle, and personality. Whether you’re saving quietly, building equity somewhere sunny, or exploring rental income, the key is finding a path you can stick with—and one that sets you up for long-term success.
If you’re not ready to hire an investment advisor to manage investments, that’s totally okay. But investing in solid financial planning advice—just to clarify your path and confirm what’s possible—could be the most valuable step you take.
David Brown was the Chief Financial Officer/Business Administrator at Blanchard Memorial School, Groton School, Alexander Dawson School, RippowamCisqua School, and Portsmouth Abbey & School over a 23-year school career. During that time, he advised and/or helped heads and administrators assemble and negotiate benefit packages that would ensure a comfortable life through “end of plan”. For over 10-years Dave has helped his clients effectively plan, save, and invest to and spend appropriately through retirement.
For personalized financial planning and/or investment guidance, contact Clear Skies Planning & Wealth Strategies at www.clearskieswealthplanning.com or directly at 720-833-8611.
Clear Skies Planning & Wealth Strategies, Inc provides advisory services through XY Investment Solutions, LLC, an SEC registered investment advisor. All views included in this communication are subject to change. Please contact Clear Skies Planning & Wealth Strategies to receive a copy of our Form ADV and other disclosure information.