I would rent the extra room(s) similarly to a medium term rental property.

What I would do is make sure you have a good long period to get a contractor in and you can pull out if gets to high.  

Even with prices going up, I still think you can find some great BRRRR deals in Cleveland as long as you act quickly and put strong offers in on the properties as soon as it hits the market since there a lot of other investors looking to do the same thing. 

I dont really see a disadvantage to investing in the self directed field other than it is not as easy to 'cash out' if you need the funds for something else, which is not always a bad things IF you are investing for the longer term, and that you can not leverage as highly as outside a plan.

They can provide guidance on potential legal options and rights concerning the city’s demands and the lender.Negotiate with the City:Seek Extensions or Variances: Your friend can request an extension on the deadline to comply or apply for variances that might allow the property to meet less stringent requirements.Explore Grants or Subsidies: Check if there are any local, state, or federal grants or subsidies available for renovating older properties, especially those providing low-income housing.Engage with the Lender:Discuss Financial Hardship: Present the case to the lender, explaining the situation and the financial hardship imposed by the new building codes.Propose a Loan Modification: Suggest modifying the loan terms, such as extending the loan period, reducing interest rates, or even deferring payments temporarily.Negotiate a Short Sale: If the property must be demolished and rebuilt, your friend can discuss the possibility of a short sale where the lender agrees to accept less than the owed amount to avoid foreclosure.Explore Refinance or New Loans:Seek New Financing Options: Look for other financial institutions or private lenders willing to provide financing for renovation or rebuilding.

It's great in terms of location, but the main issue that I have is that there is no public trashcan for the bus stop.This means that people are constantly littering around my property, and I am forced to pick up all of their trash.

My goal is to buy the house, terminate the section 8 lease as soon as possible (at the lease term, to avoid eviction process), and search myself for other better tenants.

You would want a contract spelling out the terms of the deal so everyone is covered. 

Before long JKV will be on the radar of all the major title underwriters and their title agents will need underwriter permission to close deals in which they are involved.

Should I discuss some bullet points and do a small contract between me and the buyer or is there a standard contract for such that we can agree up on terms prior to handing the deposit to the title company?