Difficult tenants tend to seek out self managed properties.  

Aside from it being a short sale and I am sure some of you know how difficult these can be, what was even more so challenging was that this property had tenants, the seller lives in Hawaii, US Bank is think is located in the mid west and my Buyer, wasn't a direct relationship but through a whole seller. needless to say thing did not go as planned, but the bright spot is simply this...

I will be getting more than 1% per month rent in a location where that can be difficult.

It is difficult to tell you which option is best without more information.  

If the LLC were in all cash, this may not create an issue, but with difficult to value assets in the LLC, what exactly is the shifted equity in the LLC worth?

Several FNMA restrictions apply plus the current lender may have their own internal guidelines. 1) How difficult is it to obtain a Supplemental? 

It is very difficult to structure a PE deal when the other partner(s) is not also bringing cash in or is in some way developing/renovating the property.

Always difficult to directly translate to value but I think it  is worth it.Also agree with other responses that I would avoid late/non-payers as well as those that are pains in the back side (for me only 2 out of 44). 

There are other good uses of old structures for firefighter training that may not help you solve your problem but are difficult to simulate due to their destructive nature such as forcible entry (ie breaking down doors) and vertical ventilation (cutting holes in roofs) that you might mention when trying to sell your idea.  

With turnkey rentals, it would be more difficult.