Depending upon that, and your financial health I would just recommend hanging tight and adding another avenue of future income.

I'm searching for an insurance professional to discuss the concept of negotiating group purchasing property insurance for a discount (similar to what is done through health care via employers).Are there regulations that would make this prohibitively difficult in the property insurance industry?

It's definitely interesting and there's a ton of investment in this space.Healthcare is huge in Detroit and The Henry Ford Health system is undergoing massive expansion.For real estate, Rocket Mortgage/Quicken Loans is a big employer in the City.

I have some ideas like giving their number out to wholesalers or whoever texts me 10 times a day asking if I need help finding health insurance, but I'd love to hear your ideas as well.

@Chris Lo not an issue unless deteriorating, which potential exposes people to the fibers and is thus a health hazard.Even then, all you have to do is properly encapsulate it, usually with paint and then put siding over it.What cities are you looking in?

Payroll, Health care, PTO, vacation pay.

This personality type tends to come back for modifications, health and safety code violations, defers maintenance. 

That's what those under-educated so-called financial expert fools advising HUD gravely FAILED IN THEIR LACK OF INTELLIGENCE TO FIGURE OUT BEFORE CREATING THIS brow-beating, emotionally-destructive, mentally painful, soul despairing REVERSE MORTGAGE INDUSTRY! 

I have had to evict one guy for non payment of rent and evicting a woman on Tues for non payment of rent and disturbing the peace with her mental issues.

Determine what he needs in his retirement and set that (mentally) aside.