How do I charge (keep from deposit) the amount of time it took me to complete repairs after the tenant leaves.

We allowed the property to sit empty for 5 months with a security deposit and signed lease for a 2-year term at above market rental prices.

Security Deposits.

Many, many times I've used existing deposits that seller is supposed to give to me as part or all of a DP.

Tenant... signed lease in December paid deposit.

The first applicant that meets our criteria signs a lease and has 24 hours to get us the first month and deposit in some form of a money order, cashiers check, wire, etc. 

For landlords in Chicago should I request a security deposit or first months rent or how does that process go?

Just like any bank they don't have 100% deposits sitting to match up to 100% of their construction loans they are cycling money. 

(Pro Tip: The security deposit is often great leverage to get them to respond to you: "Hey, Tenant.

I would think there would be risks, I think they get around any licensing based on not having to do trust accounting (funds are still deposited directly to the owner who then pays the co-host via Venmo or whatever).Your experience far outweighs mine I am sure!