I've attached the median list price for Detroit here as well to compare to something like Cincinnati. 

There's lots of definitions and distinctions between the two that get thrown around. 

Wraps cost more and take longer (legal fees, recording fees, servicing fees, etc) compared to a SubTo.

Study the original business plan and why it has gone wrong and compare it to the new business plan.

Also would love answer to the following: - Are there any specific challenges or advantages you experienced compared to a JV structure?

Today is very different as it is all about the management (and not appreciation) compared to past where management could suck but you still had superior apprecation.This will not crash housing of course but all those "creative" deals where people are paying more than market value are going to realize they have no exit. 

In fact, the appraiser may not even appraise it at $280,000 even though the comparables would point to that value all day long.

How would this compare with privy and podio?  

That's it, but a) print out a page for each property you think is comparable, b) make the list of repairs long and inclusive of everything you've done. c) Put larger items first like kitchen remodel......and don't just say 'kitchen remodel', list things like 'custom backsplash tile/Bosch appliances/recessed can lighting/pot filler/etc. d) Cite the price/value of the work done, and don't be afraid to be generous.

The way I see it is you're comparing two options, to HH or not to HH.