Was he worried, stressed, etc?

I would say if you truly think selling it to him would net you an extra $30k, then worst case attempting to pay off $30k of his credit cards would be a wash if he never paid you back a penny, and also the hassle of listing it amd rehabbing (aka time/energy) is saved as well.Just my 2 cents.

I've also had a guy that responded but didn't know what a trailing 12, proforma, or schedule E was. He

Buying at a discount will offset a good portion of the tax and penalty I pay when I cash out and I get to immediately start using the income to fund future investments -  Based on the very basic calculations I have run, in the end, it will be a wash and come out about even. the only difference being that I'm not waiting to start cashing rent checks.Ultimately, you win with either choice you make, because you are doing SOMETHING - you are investing and furthering your financial position.Good Luck and Happy Investingjeff  

Unbeknownst to many, Aguadilla is one of the handful of towns that is solvent, it has no debts and it has cash reserves.

I considered my options for an affordable home: 1) mobile home, which could wash away in the next storm; 2) houseboat, which could float away in the next storm; or 3) land-based structural dwelling, which is only slightly more permeant than the other two.The decision-tree continues... what type of structural dwelling: 3a) an older ground-level house; or 3b) newer elevated house on stilts above the hurricane floodplain.

Overall, there are advantages and disadvantages that come all out in the wash, if you're aware of them and work with them, instead of against them. 

In order for the property to be habitable, it must have all of the following: a) Effective waterproofing and weather protection of roof and exterior walls, including unbroken windows and doors.b) Plumbing facilities in good working order, including hot and cold running water, connected to a sewage disposal system.c) Gas facilities in good working order.d) Heating facilities in good working order.e) An electrical system, including lighting, wiring and equipment, in good working order.f) Clean and sanitary buildings, grounds and appurtenances (for example, a garden or a detached garage) which are free from debris, filth, rubbish, garbage, rodents and vermin.g) Adequate trash receptacles in good repair.h) Floors, stairways and railings in good repair.In addition, the rented property must have all of the following:i) A working toilet, wash basin, and bathtub or shower.

This inspector's main concern was he found a paint chip on the floor and said all the paint had to be removed for he thought it was lead based paint but didn't understand there was no paint in the hallway where the chip was found and couldn't find out where the paint chip actually came from. 

Pressure wash house, driveway, etc.24.