Who collects the rent for the 2nd unit?

There are ALWAYS unintended consequences to these kinds of laws/rules and the hubris of the govt to believe they can perfectly legislate so as to avoid anyone being harmed/hurt is what will ultimately be 'our' collective downfall. 

Collections are already becoming tough (and expected to get worse in coming months) paired with historically high unemployment.

I am collecting emails and sending them an email with the application.

I am looking to help them keep the house get it rented and renovated so they can maximize the rental income and help them get income so that they can move out and live in another house or should I have them stay in the house and just collect rent

Should I file a small court claim because she owed the rent and broke the lease without a 60 day notice (written in the lease), or should I send it to a collection agency? 

This time I told him he could be a transactional agent (represent both sides and collect double commission).

You might still have a few items like RE tax depending on when they collect it.

I might even consider a hybrid and make the tenants responsible for their own recycling which is collected weekly and then have my grounds guy come by to do the garbage every two weeks.

He insists on collecting all 60 units of rent BY HAND.