The house is well maintained but there are always a few things to be done after the green card inspection but this process has been painfully slow (our inspection was Feb 2020 and we still haven't received a report).

Culture of the group - is it established & maintained?

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." 

Whether you can use Cost Seg to accelerate depreciation and offset your personal taxes is dependent on your income level and whether you qualify as a real estate professional + materially participate (I.E. pick tenants, repair issues, maintain property) in the properties you're invested in.

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!

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.

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