So the good news is that there are currently two full-amenity condo buildings in/near downtown Chicago in prime A+ Class neighborhoods that allow short-term rentals: 545 N Dearborn and 30 E Huron.

On either an A class property or a commercial building, I would do preventative maintenance, but beyond that I wouldn't worry about it. 

@Bobby Noubiap if you invest in the City of Detroit, you must understand which of the 185 Neighborhoods are Class A, B, C & D.Otherwise, you may get scammed into buying a Class D property thinking it's Class A, B or C.We've got that data if you're interested.

These properties are in the B to A class range, 2002 built so this is the first time needing an AC system replacement.I am curious what everyones thoughts are here, would you go with the nicer system since you will have the property long-term, or is the $1,000 cost difference too steep for you?

I might be like Stuart and not charge late fees at all for high class units.

Multiple share classes.  

Be also mentally and emotionally prepared for the folks that think just because this is not your primary home, it's somehow less of a catastrophic event for you because others did lose their primary homes.That's why it's vital for you to form support networks with people who are in your same boat - ideally in the same community.This truly pains me to share - but most of the disasters I'm seeing across Western NC are going to be considered flood events and if you do not have a separate flood policy you will likely get no coverage.

@William SilvaRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?

_____________________________________________________________________Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?

I know it's most likely a block by block case but what class of area is it?