Hey @Tommy Cangelosi, I use AirBNB and VRBO to check the basic stats for occupancy and nightly rates based on what I am looking to buy.You can really get a good idea just from scanning all the properties in your specific criteria.

Stats say that the area population has grown faster than the state avg, and median income has grown but not as much as the avg.

Just start taking addresses out of zillow and plopping them in to see some rough stats. 

I don't know the stats of houses you are thinking of buying but it needs to rent at the maximum of that range or you need more down payment, also assuming there is no HOA cost.

I got these stats from the site for Columbia for example:"Columbia, Maryland ranks #10 in the state of Maryland, and #424 of 19,654 cities nationwide."

Do some research on your target area for some basic stats that you will use in your deal analysis. 

Yes of course they have meticulous stats on this once you are signed up with them.

A lot of rural listing are done using stats from the owners memory, which often isn’t perfect. 

Also, you could check out AirDNA which has great stats for short-term rentals.You do have to register with the city of Chicago, Airbnb makes it pretty simple but as @Brie Schmidt mentioned there are specific requirements to get approved. 

Also, title examining skill isn't portable.