Assuming there is not a similar program to the BC Temporary Rental Supplement Program that you can leverage.Seems like the tenant wishes to ride rent free as long as they can and feels it will have no adverse affects on them once they are evicted in finding further housing.

With the RTO, what I'd love to do is sign a standard year to year lease, and then another lease/lease option/installment sale contract that would give the tenant the property in 30 years in exchange for an initial fee or a monthly fee and them assuming maintenance, or something of that nature.

While I'm not looking to replace my w-2, I would like to supplement it and have my properties there as a backup.

I think it also depends on the amount and the nature of the deal. 

Its transactional in nature meaning if you quit flipping, your income goes away.

Typically above ground pools do not need to be fenced off as they already have a natural deterrent to someone "falling in".

Over the past 15 years, it has served as a great vehicle for saving money due to its automated nature.

Admittedly, our internal thought process has been a bit more subjective in nature and is only being shared here privately with fellow investors in the context of helping us screen tenants to place in our first rental unit. 

Depends largely on the area, and sometimes the nature of the shingle.

Long-term hold LOs and SLOs principals stay in natural persons name, acting above board, sans 'sophistication'.Lender's and title don't like anonymity, what they don't understand or lots of moving parts plain and simple.