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! 

There is also a refundable deposit of $[#,###] required.Please keep me in mind should you need to place a client in temporary housing.

The activities of wife with respect to the rental properties included, among other things, cleaning common areas, collecting coins from washing machines, performing repairs at the properties, communicating with tenants, collecting and depositing rent, maintaining insurance policies, purchasing materials for the properties, as needed, paying bills and keeping books and records for tax accounting purposes.

I could see a buyer putting up a deposit, but could you get enough to move the needle?  

Think of all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

Below are some of the issues that I find when the books are done.1) People improperly record mortgage payments as an expense even though mortgage payments are composed of loan paydown, mortgage interest and escrow payments2) Closing statements are improperly recorded3) The balance sheet hardly ever shows security deposit transfers4) PM monthly statements are hardly ever recorded properly.I do the books for my own real estate company - feel free to take a look at how they look.

The $532 vs $500, take the extra $32 out of her deposit when she leaves.