The purpose for this property will be to supplement their long term care.

Is he looking for a new job or do you plan on using the property sales to supplement your income for the near term?

This amounts to the cheapest non-government supplemented housing option.  

This is getting to know team, track record (both full cycle deals and current performance of portfolio), what is the business plan, who is managing properties, who is tenant base, what is financing structure, what happens if a supplemental capital call is needed? 

Encourage the tenant to purchase a window AC to supplement the cooling or install a heat pump for just their unit

design and renovation - cash supplements

It can also help to supplement your income while you hold your W-2 job without all of the expenses of being an agent. 

Supplement or Increase my current income with my Real Estate Agent Job Alone 4.

Yes you will need a STR compliant property insurance, there are supplemental coverages you can get where you pay by the night or reservation as well. 

We decided that neither myself and girlfriend liked our jobs, and realized that if we were to switch carriers and advance our professional careers we would have to take pay cuts, and needed to supplement our income before switching careers How did you find this deal and how did you negotiate it?