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?

The tenant called me to explain that she has a medical issue and cannot pay next month's rent on time.

Not carrying water for State Farm here as I have plenty of issues with them but a slow leak is often not covered under any insurance policy. 

If they drop the issue, they were just looking for freebies.

The companies you mention have been around for a while and have stood the test of time.They have stood the test of time in a niche called "turnkey real estate" that has always carried a stigma.So I think that speaks volumes of their quality 👍Nobody is perfect and those that work hard, will eventually make a mistake.As long as the mistake is an "honest mistake".And being a turnkey provider myself for 10+ years now I can sure say that some investors can be a true pain in the A$$ and it feels like they look for drama/issues intentionally instead of smooth sailing lolWith that said, I suggest doing your online research and reaching out to the one that tickles your fancy the most.And then go from there.Wishing you much success.

If you want to experience landlord issues, you can fha a duplex or buy an sfh as an investment property & that $250k will easily be spent. 

Has anyone performed a Rent to Purchase financing with their buyer, as opposed to seller-financing where a deed of trust and a promissory note is issued to the buyer? 

My main issue is employment history.

The issue is more people want to live in places like the Bay area and San Diego (NYC, LA, OC, Honolulu, Kona, Boston, etc.). 

My realtor did a comp search and says the home is worth about 730 with the comps in the area, I spoke to a bank in regards to Cash out refinance and I can pull out 80k (which I will use to buy another property) my mortage will be 3k per month...my only issue is that my interest rate is 3.75 on my current mortage and will be 4.6 on the refinance but will be getting rid of the fha loan.