I have a contractor that I use for jobs that are too complicated for my boys to do. 

You're over complicating this. 

Client gave me a project to do that seemed very complicated to him. 

He also states he could help in cutting down on wholesale fees, unnecessary title fees, commission etc. 

As others said, read up on local laws to make sure you and the tenants are following them.The shutdown has complicated things, but give them notice that in 60 or 90 days (longer than you'd normally have to do) they need to make a decision and give them a copy of the lease now. 

This gets a little complicated in the case of a house hack, since if you're claiming a percentage of expenses and taking depreciation you won't get the entire exemption.

Anyways, I've told them that I would pay for repairs in the future on this new fence, but I am not paying for this new fence which was completely unnecessary. 

They are much more complicated than what most resi brokers are trained to handle.

If anyone is interested in reviewing my overly complicated spreadsheet for input please send me your email address. 

If your application form asks applicants to disclose their criminal histories,  As of December 31, 2019, Cook County Must provide their tenant selection criteria along with the rental application to the tenant and landlords must approve conditionally based on their credit before requesting a criminal history and consider only the last three years of any convictions.The ordinance is a bit complicated and needs explanation.