We have let him stay for free for the last 8 year's basically supporting him, with a verbal agreement he would fix up the place.

So, my suggestion would be to get into a position where you can handle the cost of maintenance without the warranty and save yourself the extra money that you're paying. 

This was many years ago, but I was pulling in $3900 tax free for Berkeley BAH, and paying $1100/mo in rent, oh and unlike all of my classmates I wasn't going into student loan debt. 

It comes free with my MLS subscription as an agent, not sure what it costs outside of that. 

Also, calculate potential profits by considering purchase price, renovation costs, comparable sales, and expected rental income or resale value before doing a deeper dive into the specifics. 

Typically, distressed properties literally sell for Market Price - Expected Rehab Costs, so any equity gained is mostly sweat equity.

Many investors think that if they don’t qualify for REPS status, they won’t be able to benefit from a cost segregation study.

You typically borrow up to 75-90 percent of the purchase price and 100 percent of the rehab costs.

STR looks like an attractive option but I am a novice in this area so looking for input on realistic income and cost estimates of a STR managed by a 3rd party property management company. 

I've had to chaop down a massive oak that cost me about 5K to remove but other than that, not too much.