Fast forward to today, and they've fine-tuned this tool so well that it's like having a crystal ball for home values, nailing down prices with jaw-dropping accuracy.But the real game-changer is something they're calling a "housing super app."

@Issac Harris  I think @Jon Crosby nailed it and I agree with his answers.

One of our markets has a cap on the number of STR licenses with a huge waiting list and very few licenses changing hands over the last few years, so that doesn’t appear to be an option for us in the short run. 

@Stuart UdisHit the nail on the head and I would agree and have said same thingOne thing I will add is you mention contract management / this should include an attorney reviewing the contract and the investor understanding what indemnification is.

.* have identified the most likely tenants for the development in question, and understand the building criteria each have for spaces.If you haven't answered "Yes" to each of the above, I would recommend pausing until you have the above nailed down.

Same thing with pictures provided I'm not doing any damage to the home a few little nails to hang out some family photos is not something that should cause threats.

@Michael Dumler absolutely nailed it. 

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.

That's where I think you nailed it. 

Jay hit the nail on the head with this one.