Also remember the time these returns will take to amend along with the possibility of opening up audit periods/red flags with the IRS due to amendments.Doing this yourself on turbo tax likely won't be your best bet considering all of the details.

If they don't have one, I bet they know somebody.Answering your questions:1.

Yes, it could be the signs of a certain personality defect, but it just as likely could be the sign of a young 20 something being "young n dumb" making poor choices. 

I now have a few decent choices in Pittsburgh but it took me kissing about 5 frogs first. 

Rainier.There are choices, but personally I don't think cashflowing there is easy. 

Of your choices, #3 makes the most sense, but it doesn't have to be a house hack.

Most of the regs prohibit it within the city, so I would check and see if the area you are looking allow it.Your best bet is to look at the markets on VRBO and AirBNB and see what is out there right now.

It's slowly improving and I suspect sec 8 would be a poor choice.

We opted to go with a smaller renovation and it was the right choice in the end.

Commercial and multi-family real estate are great choices in Houston.Good luck!