From my experience, section 8 tenants will go above and beyond to maintain their section 8 support if it becomes at risk.  

So, you can do a land contract for 12 months, which should allow lender to credit you full value of the land vs the purchase price, but the loan will pay off the land contract, so the lender maintains first lien position.Can't help you with the rest of your question, but you should be able to search for "CPA" here on BP to find experts to reach out to.

There are also additional costs of operating and maintaining an LLC, like separate bank accounts, annual report filings, tax filings, etc.2.

Nights, weekends, holidays, etc.To keep this on-topic, though...DO figure out what's healthy for you to manage but remember it's a process where every experience teaches you good and bad (and be patient with that process).DON'T sweat the small stuff (damage/costs under $50, undisclosed dogs, etc.) but DO find a way to learn, prevent, put in better practices to maintain your sanity. 

We have created work instructions for every step of the process so we can maintain consistency in how we evaluate properties, communicate with tenants, market our properties, handle rent increases, manage property turnover, etc..... 

Start by formalizing the transition—create a lease agreement and maintain detailed records of rental income and expenses.

AND the side you live on you can rent out a room or two depending on the number of rooms in your duplex or you have the option to maintain your privacy and sanity and keep it to yourself.  

Your brokerage is required to supervise you, and maintain all records of the transaction, just like any other client. 

Sometimes the tenants are coming from shelters or other communal type of housing where maintaining a space my not be solely there responsibility so maintaining the unit may not be to your liking. 

There are also additional costs of operating and maintaining an LLC, like separate bank accounts, annual report filings, tax filings, etc.2.