There's a podcast 109 that has lots of information, but honestly, I don't plan to use an attorney out of my state. 

I am getting ready to close on my first property - it's a duplex located in the Pilsen neighborhood of Chicago, and I will be renting out the first floor unit and occupying the second floor unit myself.

But while the plan was always to house hack, I didn't spend enough time looking at what would make the best rental.

When I underwrite my deals, I plan on 5 years without a refi. 

My wife and I are both W2 and we are evaluating to buy a vacation home to enjoy it, but planning also on renting it as a STR while not being there.

The cost starts with  1.) plan cost (survey, civil engineer, site plan, architect, structural engineer, mechanical/electrical/plumbing (short for MEP) plans, etc.).

Hows the overall condition of the property > If the appraisal is marked subject to it won't be able to go conventional or DSCR It needs flooring (bad carpet) painting and there is a hole in the side of a fiberglass tub.

I planned to tell them that "I will waive the final 2 months of the lease but unfortunately I will have to keep your security deposit".

I live in California and planning to move in Illinois.

And is that where your also planning to invest?