Same facts, except that John only has 3 days of personal use in the year. 

I know that much of it is based on personal risk tolerance but any advice would be greatly appreciated. 

So now it hits a rich and famous person.

This just depends on you personally.

I personally reserve 15% of my rent per month for maintenance, capex, and vacancy.

Even though the ONLY way that a tax sale can be reversed is if the entity or person that lost the property can prove that the tax collector missed the statutory public notification laws.. ( ask me how i know this one LOL ).. 

The drop leaf table folds up for a third person or move it out for a 4th.

 Once a person lets earnest money  go hard, they become emotionally attached.If you find yourself in a situation, where there was something majorly different than what you realized, then it is my firm opinion that it is best to let the seller have your earnest money and take stage left.Remember, no deal is better than a bad deal.No, I have not always been the master of that particular principal.

I've also filed my personal 2023 tax returns and have those available with the STR income included.

I haven't used Investor Carrot personally and know many people are happy with it.