We know and trust the family and have no concern about getting paid, but we know there are risks and would foreclose if necessary.

@Ricardo CristobalHi Ricardo, It depends on your risk tolerance and your ability to manage from afar.

I have been contacted by a few wholesalers but skeptical of jumping on the deals because I do not want to put all my money at risk.

All about risk mitigation!

They won't take on your case if they aren't 100% certain they will be successful, so there's very little risk involved. 

and he asked me to send over the contract Through Email, Now I've never done a deal before, am I risking anything if I email him a contract (with my fee tied in of course) how would that go?

Almost all landlords would be insane to let a good tenant go, to just raise rent by $50 and risk having it sit vacant for a month.

Call your attorney and have them start procedings.Regarding the other tenant, you may have to release him from his obligation on the lease if he is providing reasonable proof (restraining order, police report, etc) of a risk of harm or danger. 

It's common to have an illegal basement unit in Chicago but it's obviously a risk.

Hello Carolyn,If you want to risk the opportunity of having a fair housing law suit I would move pass asking for any additional deposit on the property.