Generally speaking,,, mortgage states take longer than Deed of trust states.some states are very fast  like Georgia...

Not so much in today's entitlement society as more people claim victimization by prediatory lending, etc.

I can't speak to Chicago laws, but here in Orlando we have very specific zoning for short and long term rentals.

This question is more of, "am I entitled" to rent based on our text correspondence. 

@Chris Field  hit the nail on the head.. much harder than it looks.. sense of entitlement out there in society that creates this  " I deserve it " attitude without putting in the apprenticeship.. you need certain amount of intangibles to be successful at RE

I feel like home buyers have a sense of entitlement and would want a venue to have their opinions heard.

I would agree that the 6.5% rate isn't bad historically speaking.

If they are highly regarded locally, you can speak to other investors who have done business with them.  

Speak with other lenders.  

While I was speaking with my personal bank, they said they could offer better rates in the form of a traditional mortgage, but would cap my lending amount at a 43% debt to income ratio.My goal is to leverage my money as much as possible to maximize my buying power.