Differences in SFH Market from Chicago to Dallas for graduating college student?

[Steve Onay]

Hi BP community,

I'm a junior studying engineering and I'm starting to strategize for my first house-hack, and I hope to pull the trigger in about 12-18 months. I'm hoping to start my career in either metro Dallas-Fort Worth or Chicagoland, and my main priority to is to minimize my housing expense with roommates while building equity and learning how to be a competent landlord.

My questions span broad areas and as I continue to do my own research, I'd really appreciate any experienced investors and residents who can chime in:

1) For those who have invested in Chicago and DFW, or moved from one to the other, are there any qualitative differences in the way homeowners approach rehabs, structural issues, expenses requiring insurance claims, or any other major overhauls that a newbie must account and budget for?

2) While I live in Chicago and have a good grasp of the abundance of the duplex and triplex investing opportunities, I've heard that Dallas and Texas at large is known for its proportion of SFHs. If this is not the case, would you still recommend (as I suggested above) I start out in SFHs by renting out individual rooms on a 6-12 month long term basis?

3) Any other differences in property taxes, tenant laws (I will be doing my due diligence here thoroughly as well), and investment sentiment between the two regions?

Thanks so much for any responses in advance!