Start with a rental that has modest rehab requirements such as updating kitchens and bathrooms and make sure you qualify for permanent financing through a lending source that offers interest rates similar to that of  a bank.

Offering the property on a lease-to-own basis might attract buyers who can’t immediately qualify for a mortgage.

Not practicing law in your state though, so you need to consult a qualified lawyer in your jurisdiction to see what to do

If they want to bring on a new roommate, you screen them like anyone else and if they qualify, great- you can talk about amending the lease at that point, but that is only a courtesty. 

And THE most important thing is that you have to work with a Qualified Intermediary BEFORE you close on the property that you are selling.

A tenant doesn't qualify for a S8 voucher by making good financial and life decisions, so what quality of people do you think the system is dealing with?

I do qualify for being a broker which comes with some additional education etc. 

Or your inability to qualify for said financing if you had to acquire it yourself right, I mean, no way, of course you have financial capacity to more than qualify for the mortgage financing right.

In a tenant friendly state you have to.BTW, when you list, there's a fair housing law. you cannot deny a sec 8 if they qualify. your standards need to be the same for everyone

The most likely options are exchanging:Life insurance for life insuranceLife insurance for endowmentLife insurance for non-qualified annuityPersonally, I would first determine what type of exchange you want to do.