I contacted State Auto, and they initially said that foundation issues were covered and provided terms and conditions for that.

While I cannot speak for any of the other areas you mentioned, I can provide you some insight into the investing market here in Sacramento. 

You can also consult with lenders, brokers and ask them for suggestions on who might be a good real estate mentor and most will be able to provide one.

Do you have a good relationship with your parents and are you comfortable collecting rent from them, addressing maintenance requests for them and things like that? 

It does provide me clarity about the direction i should be taking.Thank you!

It does take some training though, which we provide.

The taxable income of a nonresident subject to North Carolina income tax is determinedby first calculating federal adjusted gross income as calculated under the Internal RevenueCode, adjusted as provided under G.S. § 105-153.5 and G.S. § 105-153.6.

I would provide the cash and backup reserves, I house hack one of the units, then she becomes the cosigner for me in order to be approved.

This is all info your local investors can provide by networking. 

For sure, it will be much easier plus more understanding on the other side provides an easier place for you to learn.Where exactly is the property at in Chicago?