So there are a few ways to look at this, the 1st question is are you sure your renovation’s will double the property value, most renovations on primary residences, your lucky to get 60-70% of the dollar cost back out upon sale, so really nail down your comps, than you have basically a math problem if your rate on your primary goes up how long if ever before that extra payment is more than 400k in taxes, that’s just a simple calculation to help you decide, but I suspect you actually have a different question here, from a purely financial perspective my guess is the best option is to do anything to avoid that tax hit, but one of the reasons to make money is to spend it on things that you enjoy, based on your overall financial picture and a subjective view of how much enjoyment you will get out of a renovated home, you should decide if you want to roll your profit into another deal or “cash-out” your winnings, I love cars and I’m willing to spend more than is fiscally smart on them because they bring me joy, there is nothing wrong with that, but i don’t think it’s a fiscally smart choice, without knowing your exact property id imagine a renovation would fall into that category, so that’s the terms I would use to decide.

How is that not a win/win for the GC?

People learn much more from others challenges, not the far and few between wins that went as planned. 

They made good money and maintained my properties and I collected above market rate rent, win-win.

It may be your right to do so, but you will win nothing here for it.

Awesome—what a win. 

Win-Win for all of us involved.

I was so happy to have access to a Connecticut lease agreement and other key documents with my Pro membership. This saved me tons of time drafting these documents from scratch. Note however, as of October 1, 2023, Con...

You get to be creative and come up with win-win solutions.

For small claims, even if you win, you are unlikely to ever see the money, so I wouldn't bother.