The Thought I Have Every Summer
I'm going on vacation soon to visit Lake Michigan. And every time I go, I have the exact same thought:
Maybe I should just buy something out here?
I moved to Michigan in 2014, and somewhere along the way the western side of the state got its hooks into me.
The dunes, the water, the fact that Lake Michigan feels like an ocean if you squint a little.
My family has started making annual trips out there, and I can easily imagine us doing that for the next twenty years.
And so of course, when we book the trip and the money exchanges hands, I'm reminded that I'm paying to access an asset that someone else owns.
And they are profiting off my desire to be there.
Which inevitably leads to the question:
If we're going to keep coming here anyway, should I own something?
The Fantasy
The pitch is easy to sell yourself on.
Buy a place within walking distance to the beach
Use it a few weeks a year
Rent it out the rest of the time on Airbnb or VRBO
Hire a property manager to make it hassle free
The result? You get free vacations, extra spending money, and an asset that grows over time.
Of course, this is the optimistic picture.
The Reality
A vacation home isn't just a vacation home. It's a capital allocation decision.
Every dollar that goes into a beach house is a dollar that can't go somewhere else.
And here's where it gets complicated: because this is a lifestyle investment, it can never be a pure ROI play. The goal isn't maximum yield. It's whether I can make my family's life better and make the numbers work at the same time.
That's a harder test than it sounds. Because the moment you factor in how you actually want to use the property, a whole layer of hidden costs start to surface.
Property management fees
Higher wear and tear from rotating guests
Planning for future capital expenditures
Off-peak months where the calendar goes quiet
The weeks you pull it off Airbnb because you want to be there — which happen to be the same weeks everyone else does too.
The frictionless fantasy is far from rugged reality.
Still, that doesn't mean you abandon the dream. But you need to do your research.
Lots of research.
So Here’s What I’m Doing
This is the first in a series where I'm going to document the entire process.
The research. The assumptions. The tradeoffs. The spreadsheets. The mistakes. And maybe most importantly, the reasons I decide to do — or not do — something.
I don't know where this ends.
Maybe I find a property I love and buy it
Maybe the numbers don’t support it and I pass
Maybe occasionally renting a place for a week every summer is actually the better deal.
Anything is possible.
The goal isn't to justify a purchase. The goal is to figure out what the best decision actually is.
Your Turn
I'm curious: have you ever seriously considered buying a vacation property?
Did you pull the trigger? Did the numbers work? Or did you decide it was better to keep renting?
