Trying to avoid the cap-gains by renting it out is not a smart gamble. 

Why gamble an entire year full of problems and headaches over 120 dollars or whatever you are trying to save yourself/them?

I understand the small claims court route which is a tedious process and plus a gamble specially since i have to pay out of my pocket to initiate the process and there is no guaranty he will pay even if i win.

If you receive a $1,000 in rent you have a $1,000 in income (before you subtract expenses,) the irs doesn’t care if you deposit in in the checking account, gamble it away, lose it to a pick pocket, or literally light it on fire. the only advantage to putting the extra cash in a separate savings account would be to prevent stolen/fraudulent checks on a large account but I live with that risk and sleep just fine. 

Stick with the world gold standard in a Cook Islands Asset Protection Trust or the hybrid Domestic Component Bridge Trust if you don't have a reason to go purely offshore by using a connecting "migration" clause. 

It was a more of a Gamble for me.

I suspect gambling and chemical dependency were an issue. 

My advice is don't gamble on the economy.

Should I go with my gut feeling sell at 150k or put in the extra time and gamble that it will sell a little over market value? 

return=https%3A%2F%2Fwww.courier-journal.com%2Fstory%2Fsports%2F2019%2F09%2F11%2Fsports-betting-kentucky-odds-improving-gambling-comes-state%2F2269931001%2FThis will help the economyy in plenty of ways.