With that data and consideration of the current state of things in Chicago-land, IA just being IA (lol) I would say of that list it is a no brainer, MN stands head and shoulders above. 

This also does not include tax or a cleaning fee (these are most often quoted outside your rental rate anyway).Most vacation places seem to have 3 months high season, 2-4 months shoulder season, and 5-7 months off season.

I'm currently living with family due to a shoulder surgery thats left me currently unable to work.  

And it has the added bonus of placing liability for fund security also on the shoulders of the bank and by extension the FDIC.  

If it's a multifamily Commonwealth is who I use, and though I have only worked with them a few months, they are head an shoulders better than the last PM I had.  

Hello John, Having a good agent to assist you will take a lot of weight from your shoulders.

They’re not going to be 100% accurate (airdna is probably head and shoulders above the rest) but that’s where I would start.

I got the cold shoulder whenever I brought up investing.

They pretty much turned a cold shoulder to me and said figure it out myself with the construction company they set me up with. 

I would network at REIA meetings, etc. to find an experienced local investor for whom the numbers are working (I guarantee you they are out there) and look over their shoulder to see if they are doing their math different than you are, or perhaps they are working on a completely different equation than you are.