Driveway is crumbling in multiple location, in my opinion it would need replacement in the future.

So if I do a couple deals with either FHA or a DSCR or something more up that alley… the more likely I will be in the future to qualify for deals that are more structured with OPM/private money/hard money? 

With an end to the construction on 36 in sight, maybe it'll get better on the north end (stop laughing, fellow Denverites), but the south has been a mess for the 10 years I've been here... was probably a mess well before that, and will continue to be a mess well into the future.

But it really depends on your goals and future plans.

That's the easiest, least expensive way to get started and investing in that way in your local market will have a much greater impact on your financial future than buying a cheap house in the midwest- those "cheap" houses tend to be very expensive. 

Also, to make your money go farther, cutting down closing costs is a great way to do that, We can help with that, which is why we offer 1 point Origination Fix and Flip loans.Is sounds like you already have a portfolio, you may want to look at refinancing your existing portfolio to free up cash for future purchases, the buyer's market is only going to last so long as these interest rates are being cut.

I charged them 1 day late rent fee and asked them to make sure any new accounts are verified prior to the 1st in the future.

For jobs like this in the future I plan to run as owner/builder and hire/schedule subs myself.

What assumptions are they using for future rent growth? 

I currently don't have anything attached to my illinois llc but may in the future