As far as health, I'm healthy enough and plan to seek health care in a country where it is cheap when the time comes or even getting citizenship in another country and getting health care completely free?  

As most places the health care, colleges, public schools K-12, city jobs, retail, hotels are stable. 

At 50 years old and 23 years in my career, I'll stick around to get the pension and life time health care (not free).

I work in healthcare today, so I've got a bit of understanding there).

So I am hoping we can get some seasonal rental in the healthcare profession to rent the room out too or find students to sign a year lease with a co-signer.

"As Vice Money puts it, "American marginal tax brackets aren't too different from Canadians', yet [Canadians] get universal health care and [Americans] don't."

As the founder of a security consulting business specializing in Healthcare facilities I've given them some pointers on some ways they could secure their properties. 

I've seen some case studies on independent to AL conversion. What about the opposite direction? Trying to make a plan for unwinding services and meals and just operating on rent.

However, this is not my primary focus as I am more interested in incorporating it into my Healthcare residential business but for now it would be a start.

Question - since it sounds like your wife is currently full time but you mention she might possibly take the part-time, while you focus fulltime on real estate, would health care coverage still apply through the part-time?