I have a few concerns that I wanted to get people's thoughts on. 1 - Selling a quadraplex 10-20 years down the road seems like it may be challenging as the market for that type of asset is small.

The trustee, borrower or bank can ensure you get your hand slapped hard for approaching the circumstance as a work-out or foreclosure fix it guy without a license or being an attorney.Let's say that we can approach the owner and be in compliance, which you can.You will not purchase a note as an individual investor from a bank that has started foreclosure by making an offer like that.You get a request from the borrower for the bank to sell the note in lieu of payoff as demanded.

but it will still be challenging. 

You might approach your previous lender and explain the situation honestly but tactfully.

Always approach as a developer with a specific usage.  

This decision not only maximized immediate profits but also enhanced positioning for future investment opportunities, demonstrating adaptability and a forward-thinking investment approach.

You’ll often see sales with 100-200% swings within the same area, which makes having deep local knowledge and understanding the nuances absolutely critical.I do this for a living, and even with experience, comping in Detroit can still be challenging.

Then use the extra roommate rent income to pay down your mortgage and look to refi to a lower payment in the future (3-5 years) - so it cashflow when you move out.You could also choose the smaller unit and STR the other unit to generate more cash to pay down your mortgage and refi, so it cashflows when you move out.Bottom line: you'll have to get creative to solve your cashflow challenge!

Thus, they are appraised as such - valued based off the sales comp approach - i.e how much have other similar single family homes sold for?

Learn from every single challenge.