However, we are running out of time to get this place sold as it's under a reverse mortgage and the family member is in poor health and needs to live elsewhere.  

But having a W2 would be for vacation and health insurance and a stable paycheck.

UC Health is building a hospital there and the town hall is talking to Whole Foods about a location there.  

Remember asset protection attorneys are humans and have a business to run their business is to sell you asset protection .. so if you talk to one of course they will recommend you have asset protection can't hurt you...

that's tough because i'd want to be "humane" about these things. but i'd hope he has friends or relatives that he can stay with because i'd tell him "sorry, you have the leave because there is a mortgage payment associated with this place and the bank wants their money".

We did most of the renovation ourselves on weekends and evenings and got it ready to rent in 4 months.     2nd rental was purchased the next month but took 9 months to get on the market (6 months to renovate interrupted by a family health emergency for 3 months). 

Job growth has remained widespread, with recent gains in education and health services, retail trade, and financial activities.

The property does have defer maintenance and he manages himself and he wants to get rid of the property because of failing health.

If he is so concerned about his health, he would want to move.

Not to mention the health risks.