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.

Did you properly screen your applicant?

Make sure the buy out agreement is worded properly though so it is not a prepayment of rent that will be due in the future.You must refund the security deposit or provide an accounting of sums deducted from it, within 60 days of lease termination.

Either way...costs have SKYROCKETED in the building material space...people who are building at such a low fee are likely their own GC and not paying themselves properly@Alex L. - What prompted the purchase of the lot? 

You will need to understand SEC law and how to create a proper PPM.Hopefully that helps explain why I said the question was very broad.