Repossessing a house is not like towing a car.

Its nice to have the little stuff taken care of, but I'd get bids on larger repairs rather than automatically going with their guys.

Point is, if I were to purchase the property, legal as it may be, that leaves me the buyer with a large problem on my hands (not to mention all the clutter that was apparent (old frig, busted up TV, two wrecked cars, etc.). 

IMHO I think the draw to the Poconos is it's proximity to two monster metropolitan markets and their middle and professional class who may prefer in many cases to tone it down from places like Miami, Hawaii, Vail, or Stowe, and instead have the luxury of a 1.5-2 hour car trip to somewhere where they will save on airfare, get a good deal on their accommodations, and still have loads of fun with their families without having to deal with exorbitant vacation costs and aggravating travel arrangements. 

With all the random cars that keep showing up to the house for 10 minutes a pop and then leaving and it being all different people I think this could be a drug problem. 

Like I pointed out that as part of his application process he had to provide proof of car insurance, and he blew up at me and threatened to look into the legality of my practices.

Well, when you let an 8yr old take the keys to the car, who's the idiot when they smash it up. 

Now a landlord (and architect), I wouldn't build out the space without the second stair since it really is a safety issue/liability (especially in case of a fire) if anything were to happen.Full excerpt of building code below:According to the Chicago building code on egress requirements, the third story above grade plane within a dwelling unit [which in this case is the duplex-up unit], all the following conditions must be met:1.) the building is equipped throughout with an automatic sprinkler system2.) the floor area of the story does not exceed 1600 sq ft3.) the dwelling unit has an exit that discharges directly to the exterior at the level of exit discharge.Your third story attic space is unlikely to exceed 1600 sq ft, but you'll probably find the sprinkler system to be cost-prohibitive.

Just like you can fix your own car and YouTube your way through it's not for everyone.

If you're applying for a Conventional/FHA/VA/ or USDA loan, then they will do a "global cash flow" where they take into account your PITI (Principal + Interest + Taxes + Insurance (hazard and flood) on all properties (second mortgages included), HOA payments, car payments, student loan payments, credit card payments, and installment loan payments in the numerator and your gross income in the denominator.