Not every state or city mandates that any landlord has to accept Section 8, because the landlord has to not only subject their property to Section 8 inspections, rules and regulations, they also often have to separately arrange for the tenant to pay the non-covered part of the rent and can face difficulty evicting just based on that.

If you are living in a place that is satisfactory why not change the arrangement with the landlord?  

The arrangement works out fantastically, as all parties can now do what they're best at, and while we are separate entities, our services are integrated.  

I'm absolutely not interested in leasing fast at all and I'm extremely picky about tenants and I do things like require a large security deposit (even for section 8 renters, I have three of them and love them), don't supply appliances, take my time doing background checks and arranging multiple calls/meetings with potential tenants. 

@Chris Johansen I believe the part you're missing is you are not "simply loaning him money" under the new iteration of your partnership arrangement.

I could have bought it and arranged to upgrade the panel on Day 1 after we closed but I didn’t feel good enough about taking the risk on a $280,000 deal in the event there was a problem and I had to try to make a claim prior to the repair.

Make sure your listing is well optimized you can also do a little tweaking to your listing daily to get on the algorithm, make sure your photos are eye catching and well arranged, you can send out your link to friends and families and ask them to add it to their wishlist.In terms of pricing you always want to start low to get some bookings and ratings then slowly increase your price.I wish you the best in your business.

"If you don't believe you can clean up after yourself this isn't the living arrangement for you"!

Because they got a cute arrangement that wasn't understood on both sides, it's just a waste of time. 

I don't like this arrangement that she is in another state but paying rent for her son probably because her son is not going to be qualified to get an apartment.