We're based in Orlando, manage long-term rentals 1-80 units, and own/manage 48 units ourselves, so we know what it's like to be an owner and a manager. 

Long term a an investor.

I'm on my own mate.Columbus Cartel didn't accept my Gangster application hehe

Tell the tenant that his opinion carries zero weight, so he must submit proof from an ACCEPTABLE expert to support his alleged foundation issue.Until then, he will be held liable for the terms of his lease, to the fullest extent of the law.

I wonder if the investor (rent to own) will accept RRSP as a down payment.

The house was an inheritance from a trust so not a sale and not on good terms with the other parties.  

Even if you go the private money route that you mentioned (which also makes sense) - I'd advise speaking to a few HMLs at least to get comparable "market terms"

Decide on your readiness financially and risk tolerance before developing an investment plan that is comprehensive but is able to grow into a long term wealth purpose.Good luck!

The short term rental loophole is for rentals where the average stay period is 7 days or less.

The bad thing is, you are around your tenant a lot :) Get the terms and conditions in writing.