You can do well with them, but not if you allow the building/resort to manage the rentals. 

You should be asking for advice on certain assumptions, NOT if it's a good deal or not. 

You buy your family home because you want to live there, like the amenities and the only thing you think of is the mortgage and taxes, not if the rent will cover those and other expenses.

Mainly in metro Chicago as you mentioned and we work in almost all areas of Chicago.Also just FYI if you use @ and name the person you a responding to will get a notification. 

Confusing as to why landlords are not aware rent is officially "late" the day after it is due and the landlord may immediately proceed with appropriate notification.

As any number of folks here can attest to, it's not if a market will fall, but when.

Generally investors have at least some criteria to narrow down the scope, so they would at least get immediately notifications for properties fitting that criteria.

I probably would not be where I am not if BP did not exist!

I'd explain why I say that, and many here understand the meaning behind that one word, but it will mean more to you when (not if)  you learn the meaning of that word, and how it relates to your current situation, on your own.Second, your initial answer (and continuing one as well) is partnership(s). 

You have however not provided any information regarding whether the tenants rent is at market or not.