I like the idea of it being a very Red state, nature activities all year round and I think that areas like this are scare and will continue to appreciate if they continue to keep their beauty and policies. 

I have personally done both sides of things; ran PM biz grass-root's, and ran PM brokerage in a franchise system, a big BIG name one. 1 universal truth that stands in BOTH is your primary existence as a PM, franchisee or grass-root's, is that your a full-time "vanguard" of defending against the "WTF's" and in being a "Fire-Fighter" putting out the "fires" of the various "WTF's" that happen.     

Red states don't mean you will never evict.

This doesn't necessarily mean more tax, just more red tape (and definitely a higher fee from your CPA).

Never send money in advance for their fee's  NEVER. thats a huge red flag that they are just out for fees and are fake lenders.2. bad or not really good written english .. on the phone they sound like they are off shore ( which they are ).3. rates  lower than market most of the fake lenders will advertise 5% rate that does not exist.4. insisting you pay for mortgage insurance  there is NO mortgage insurance on PML HML loans does not exist.While NMLS registered and state licensed is a good way to vet a lender keep in mind only 12 states require it.

I think they are rent capped by the government (I wonder when that runs out), so raising the rents is probably not an option, and having experience in this niche with all of it's "Red Tape" and paperwork would be helpful.

Is there anything that stands out as a red flag, or perhaps there are areas you think could be worth negotiating on?

I am curious as to what root causes have decreased the Chicago inventory more than other major cities. 

Too many red flags here.   

If someone is refusing to show their ID that is a red flag.