Milwaukee born and raised—I currently live in Madison but I still travel to Milwaukee frequently and its where my family and real estate business is.My faith in Jesus Christ is a huge part of who I am and guides everything I do.RE InterestMy Real Estate Interests currently included, small multifamily buy and hold, house flipping, house hacking, and BRRRR.

Pretty unreal.At some point, this house of cards will collapse.

Address the leak immediately, once the house is water tight get everything dry and then you can approach the cosmetic repairs over time. 

And that educational out, you know, where you get a degree that offers you upward job mobility, where you move into a big house, and you drive an expensive, late-model car? 

Depending on location they can cost a lot to replace but when you factor in what you save from paying sewer bills it’s cheaper in long run.It would not stop me from buying a house

Thereis  too much info for here but given your stated information, I'd do the chapt 7, save what I can, and move on.If you mentioned you owned a house, the recommendation would be different.

So if you are looking to house hack in N Dallas, I would focus on a value add SFR you can get under market, perhaps. 

I am closing on a house and family member of the owner is living there, who has no lease, or should be in the house once I close.

EDIT - The house itself is a bit boring IMHO.

In-house engineers: The best firms have specialized engineers on staff, not just hired contractors.