As we were heading into the deep red zone, we decided to try and short sale 4 of the properties, and we moved into the 5th one ( as we had just recently got married and before we were doing the room mate thing with others).

With all the improvements, I'm estimating the house value to be around $275K (conservatively).As I mentioned before, I believe her appraisal value is inflated, based on the avg. house value per square foot in this city and based on recently sold houses with similar features.

if that's not a red flag, then what is? 

If in town, prefer quieter E end of Liberty, W of square preferably.

The square footage of the additional space is larger than the square footage of the existing 4 units.  

Im def towards the high end in terms of price per square foot.  

It was a red flag that the only heir lived very close by and was not probating the will with respect to the decedents home. 

Maybe trade work is significantly more expensive in Ohio than in Tennessee but I had a 1500 square foot property painted a few months ago and it cost less than $1000 including paint.  

Like you said @Gideon Sylvan was something that a hard lender wouldn't do so that should have been red flag number 1. 

http://www.businessinsider.com/tuscan-castle-lists...The amount of space is crazy!  This would be like living in Camelot!  I would love to walk through this place!!!!  This would be great as a hotel!