@Steven Hamilton III reached out by email to arrange a consultation with you about the information below, but I also post it here in case you want to reply publicly so the response may also help others.

I have clients that have these kinds of arrangements, and while it is easier when an org fills your units, you can lose control of maintenance and cleanliness.

There's a lot you can do remotely such as listing on websites, pricing strategies, arranging/order supplies, guest communications, going to the property and doing work on it (note: travel time generally doesn't count).

Not following the requirements (within Seattle city limits will likely have additional rules and regulations) opens the seller up to liability.Additionally, the seller always has the option of offering "cash for keys" arrangement but be sure that no funds change hands until after the property is vacated and locks are changed.John

Would likely have to have a larger plot to account for growth vice a vertically- scaled arrangement (I'm thinking like condominium-style where the real estate is multi-story).

.- You close on December 10th- The property is in great shape and does not need any significant repairs- It only needs some paint touch-up and changing a couple of broken fixtures, which you do yourself- You spend the next week buying furniture, electronics and supplies and installing/arranging everything yourself- You also roll up your sleeves and scrub the toilets and sinks and appliances- You put it on AirBnB/VRBO and have your first guest renting it for the 3 days of Christmas- You second guest rents it for the following weekend and leaves before NYE- You personally clean and restock the place between these two guestsCongrats!

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.  

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 the amount was substantial, I very well might make a payment arrangement with them. 

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