You have to consider will it be a primary, Vacation home or investment.

I will definitely continue to learn and ask questions with everyone here and I am about a hour north east of Chicago so I can't officially say I'm from Chicago but I do say I am when I'm on vacation. 

Hey @James N Beliak look into RBC's Vacation home mortgage.

Nowadays I use what I've learned and help investors building their rental portfolios in class C neighborhood while personally I either build Padsplit in class C or build high end vacation rental in class A area and hold them. 

For cleaners, also check vacation rental hosts Facebook groups.

I have restrictions on both that do not allow any sort of "vacation rentals" and a minimum 6 month lease requirement.

But for those that just host for a hobby or personal vacation home and not a business, would be out of place in such a setting! 

You can buy a Vacation home out of the state and only need to put 10% down. 

(Max vacated rents - your monthly mortgage payment) = +/- net cashflow.

Henry Clark is absolutely right, keep it legal, professional and provide a 30-days notice to vacate (preferably via certified mail).