As usual - I agree with Wayne...a LOT of cooperation is needed from the seller to make a short sale work, including lots and lots of her financial documents, continued updates to such, her listing the home, making the home available for BPOs,  signing lots of agreements, coordinating closing, possibly her being asked for a contribution if she has assets, etc etc....

While benefiting from a great location and solid bones, and a good rental history, there is no denying that the dearth of inventory and the general frothiness of the real estate market must have played a role. 

The history for it was 15k as is.

Run that, and the worst-case scenario, and the numbers, by a more seasoned investor with experience and documented success in the asset class.

When the title company, escrow agent or attorney prepares the closing documents, they simply factor in the second mortgage payoff amount into the final distribution of funds to the seller.A second mortgage should have little or no effect on a homeowner's ability to sell her home.

I was only ever told by a neighbor that there was “some kind of underground drainage put in”, however no searching of permits, city documents or anything else proved that.

I liked my old client/boss and we have a lot of history together.

You'll sign documents at title saying you understand its a federal offense if you lie about the occupancy status.

You would have ongoing filing requirements with the State and would need to keep business records and documentation.

And truth be told he is a little crazy but seems in my experience some of the most successful people in history were a little crazy. 😜