So you'll have to do your own due diligence on what to expect for rent- the vacancy rate used in calculations will be higher than the average for Chicago; You'll have to take do some homework on the cost to maintain.

There are three main categories to consider:Confirm identityDo they pay their billsWill they maintain the propertyConfirming identity includes a government-issued ID with picture and knowing how to spot fakes.

When you put your focus on what you bring to your buyers, and maintaining real relationships with them vs them just being "on the list." 

I am not a full time real estate investor and have a day job.

I would maintain a good liability policy and if a good opportunity comes along pull money out of the investment to fund the next deal!

I’m a part timer but wanting to invest in real estate market here in japan.

Have you done a blended deal, where you maintain your original mortgage and take a HELOC instead of remortgaging the entire thing? 

My money will go farther in places like Charleston but also be harder to maintain tenants or flips may stay on the market longer.

I will occasionally rent to young professionals if there's a vacancy to fill, but given the location I am able to get students in most of the time. Renting

The more you maintain your vacation house, they better you will do.