IMHO in order to secure the best terms, you'll want to stick with W-2 for the purchase.

I’m looking to buy some single or multi family units for long term rentals that would provide at least a moderate degree of cash flow.  

We went 'against the grain' of the typical cabin in the area - which are typically all wood, rustic and have not had much updates in many years.

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.

If it’s a completely separate unit in a multifamily, typically tenants are responsible for utilities to streamline your costs as much as possible.

You learn what to look for, how to bid, what things typically go for etc.Go to an auction, see how it works, talk to people who are doing it and ask questions after the auction is over or during lunch.

We have had a Strctural Engineer out to the property and while we don't need to conduct repairs within the next 5 years or so, we will need to address both of these things at some point and it will likely cost us about 100k.Any advice on selling or holding for the long term?

There is some complaints about the smell but that is fairly typical for memory foam when they are first opened up.Others have said you really have to wait at least 72 hours for it to fully expand before using or putting anything on it.EDIT - This is a special buy and has 2 days and 14 hours before it expires. 7% have been claimed so far.

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.

Typical low life tenant thinking they'll get a payday.