The most recent time, she was cooking in the kitchen and he walked right in the door.

I have heard of some HOA fees changing over time so you want to keep this in mind and make sure that you have enough meat on the bone in regards to cash flow before moving forward with a deal like that. 

I am attracted to this route because the property can be mine for $1,000 cash, and the rehab budget would put me at retail price, *AND* I will have the peace of mind of knowing that I have essentially a brand new house.

I bet if he called a property management company it would have cost me at least $100 for someone to come out and redo the plumbing that he removed and replaced for me behind the sink. 

For me at this point on my REI journey my next project will probably be all contractors and subs.

House hacking is something I'm familiar with but not really an option for me at this time being married with two young kids. 

Less expenses, today the property would cashflow for me at ~$525/month.

You are paying way to much, not enough meat on the bone for $5,000 in equity. 

A properly drafted plan like the a (FAPT) Cook Islands Trust or its hybrid Bridge Trust are virtually impenetrable to a judgment creditor.

If druggies have been cooking meth in it, all bets are off.