The $100K Problem Just Became a $15K Problem (Here’s How)
The $100K Problem Just Became a $15K Problem (Here’s How)
ByeByePool Founder Diary — May 2026
A few weeks ago I wrote about scaling back. Should I remove my pool? Spreading the big home improvement list over a few years instead of trying to tackle everything at once. It felt like the right call at the time, but honestly I was still looking at the numbers and feeling a little queasy.
Then something clicked.
I stopped asking “how do I pay for all of this” and started asking “how much of this do I actually need to do right now.” Different question. Very different answer.
Here’s where I landed.
The Windows
Original plan: replace every window in the house. That quote came in around $20,000-$25,000 depending on who you talked to.
New plan: replace the three front windows. The ones people actually see. The ones that are drafty and visibly aged. The rest of the windows are fine. They’re not leaking, they’re not failing, they just aren’t new. That’s not a crisis.
Three windows instead of fifteen. A fraction of the cost.
The Siding
I was quoted $37,000 to replace the wood siding. And I kept hearing “wood siding is a liability, vinyl is the future” from every contractor who walked the property.
Here’s the thing though. The siding isn’t rotting. It’s not failing. It’s wood, and it’s tired looking, and it needs attention. But the attention it needs is scraping and repainting, not replacement. Old wood siding that’s properly maintained can last another 20-30 years. I don’t need to replace it. I need to take care of it.
Paint job instead of new siding. Done.
The Deck
The deck needs work. That’s not a debate. But the work it needs is structural support and a fresh coat of paint, not a full rebuild. A contractor came out, looked it over, and confirmed the bones are solid. The issue is a few support posts and some surface weathering.
Re-support it, clean it, paint it. Move on.
The Roof
This one stressed me out the most. Nobody wants a roof conversation.
But here’s the reality: it is not actively leaking. The quotes I got were in the $12,000-$18,000 range for a full replacement, and the honest answer right now is that I don’t need a full replacement. The fascia boards are deteriorating, the gutters need work, and there are a handful of shingles that need attention. That’s real money, but it’s not a full replacement. Not yet.
Repair the fascia. Fix the gutters. Address the problem areas. Keep an eye on it. Tackle the full roof next year or the year after when it actually demands it.
What This Adds Up To
A few months ago I was staring at somewhere between $100,000 and $150,000 in work and wondering how any of it was possible. Today I’m looking at roughly $15,000 that addresses everything genuinely urgent without doing work the house doesn’t actually need yet.
That is not a minor shift. That’s the whole game changing.
And Then There’s the Pool
I’m not removing the pool this year. I’ve written about that decision already. But what I haven’t fully talked about is what that decision is actually worth.
Closing the pool instead of running it saves me somewhere north of $5,000 this year. Chemicals, electricity, cleaning, opening and closing service, repairs I’d inevitably have to make to keep it operational. Gone. Because the pool is closed and sitting there doing nothing.
That $5,000 is now sitting in my pocket instead.
Which means I’m building toward pool removal, not delaying it. This year of not operating the pool is the test. If life without it turns out to be fine, and I strongly suspect it will, then spring 2027 becomes a real target date. The money I’m saving this year directly funds that project.
If I had tried to remove the pool this year on top of everything else, I’d have been stretched thin and probably made worse decisions across the board. Doing less, intentionally, is what creates the breathing room to do things right.
The Bigger Point
There’s a version of home ownership where you let a list of projects grow into a number so big it feels paralyzing, and then you either do nothing or you overextend yourself trying to do everything.
Neither of those is the right answer.
The better question is: what actually needs to happen this year, and what’s just noise? Strip out the noise and the number gets manageable fast.
For me, $15,000 is manageable. $120,000 was not.
The house isn’t going to be perfect this year. That’s fine. It’s going to be better, and I’m going to still be financially functional at the end of it, which puts me in a much better position for everything coming after.
Pool removal included.
Following along with the project? The full diary starts here. If you’re in the same position — a pool you’re questioning, a list of projects competing for the same money — get a free quote and see what removal actually costs in your area. It might be simpler than you think.
