I ran a chain of restaurants before I go into real estate. 

If current owner wasn't able to pull it off I'd find out where was the issue-is buy and hold not his niche (builders at times have this trouble running 2 businesses), Are the tenants not complying with the owner, Age of the property (older it is more maintenance to keep in reserve) etc. if you want the deal then as fellow investors mentioned is to have an inspector complete a thorough inspection & run your numbers accordingly-as long as the big ticket items are taken care off then it comes down to on going maintenance/repairs & property management.

He will have wasted his time - which is something I ran into frequently as a Realtor working with flippers.You should be there with the GC when he does his inspection. 

Selling each unit would be interesting since that removes ongoing responsibility, but i am really curious what an appraiser would come up with since there is only one comp and it’s in a much more upscale location. 

We've held off on going the securities attorney route but it may be time to and allow outside accredited investors in our deals.

I am working on going through the forums now as that seems to be the general consensus.

Im on my second live in flip, and do all the work on that one myself, my other rehabs currently ongoing are completed by contractors. 

You need to have a reserve for ongoing maintenance of your properties.

WIth your on going claim, check with the agent to see if that will be an issue on rewriting to a the Dwelling/Fire policy.

Then you have to subtract for the ongoing maintenance and repairs needed.