:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+, zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680, some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Maybe you can calculate proper lawn watering costs and give the tenant that amount as an allowance.

Emphasize that if they are experiencing illness, its your priority to make sure their health is not affected and the only way you can do that is if they vacate the unit so you can properly and thoroughly mitigate the issueThis is  shakedown.....Damage to their shoes etc.... that's what renters insurance is for... not your problem.Mold remediation....90% of that stuff is a frickin scam.

Also come up with exit contingencies, if you have a balloon due IN X years and for some reason you can't pay the balloon off at the proper time.

Does the garage have proper firewall protection and heat alarms for whoever is sleeping there?

As for the practical concerns, in the dead of Summer, you have to be extra cautious about treating AC maintenance properly, because it can be dangerous inside a home that is not cooling properly, not to mention create conditions for mold growth.

@Ran Fridman it is a good idea in Chicago proper to move away 100% from security deposits.

The Led paint thing ( scam) is nothing, just do the reno properly 

I read through the rules on the HOA and it clearly states vacation rental guests can use the dock slip if I have one to provide them however I just want to make sure I'm setting it up properly so neighbors/other boat owners don't get upset with multiple guests each month using it if it ends up being a popular request.Anything helps!

I would maybe use 20-30% of it, get it to LTC gains, pay off your consumer debt, and put some more cash away to invest properly. 1 property every 3-4 years is doable, and not behind the curve.