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?

Be patient, save more, buy a smaller place, move somewhere more affordable, get other streams of income, house hack, cut your expenses. 

I moved from Florida to start investing in Columbus due to the same reason.

With all that said after closing costs, origination / underwriting fees, etc. if seem very difficult to get things moving along.

Get to know each other, and after a few deals, you just might find all the funding you can use.Keep investing and moving forward!

Here in Houston most of the 2 to 4 units are around Downtown area and if you want to find anything that stands a chance at cash-flowing after you move out, you pretty much have to look in the east side of Downtown.  

I got rid of all my rental properties when I moved away from my hometown.

I'll understand if you choose to move out, although I hope you won't..."

Hi Everyone,I'm currently active duty military about to move to Colorado Springs in the next 3-6 months and I think I'm ready to make my first investment.

Rent it for a year or two and then move in.