A realtor who used to have a PM company called "JBS Realty" until this month.He used to manage 8 of my properties and is currently refusing to pay out multiple 5-figures worth of rents/property reserves/security deposits/unpaid utility bills owed. 

We embrace S8 applicants, but screen them just like any other applicant.Many have an entitlement mentality and try to leverage their S8 voucher by pretending to be helpless:1) A percentage won't apply because they expect a landlord to waive application fees for them.2) Many cry broke and expect a landlord NOT to charge them a security deposit.3) Many of those same S8 tenants trying to avoid paying a security deposit, won't make an effort to call the list of nonprofits we send them that will pay their security deposit if they apply.4) A lot of them try to avoid paying for utilities.

Yes, you can deduct the 8 days rent from the security deposit.

We have a modest security deposit collected up front along with 1st month's rent and the cleaning fee.

Certainly one account for each LLC, (separate for security deposits based on your local rules)

Would it be a good idea to take a deposit to secure the deal until the rule clears?

Furthermore if they are always paying they probably will stiff you in the end if they know they aren't going to get the deposit back. 

Please consider this if you move forward.Additionally, you need to have a broker on payroll in illinois and three separate bank accounts with the security deposit trust account located in illinois.

Operations and Security Deposit accounts

Now, I'm imaging a scenario when every one of these tenants move out that I'll be paying their entire security deposit + interest even if there are damages beyond normal wear and tear.