Even then, we would charge unused fees to ensure that we collected enough income so the deal made sense.

He is doing all the needed reno/repair and offering a 1 year warranty to ensure that we are really minimizing any extra upfront cost outside of down payment and closing.

Should we have the remaining tenants go through a tenant application screening to ensure they meet income requirements, and other factors? 

While the rent control laws are enacted, and the tenants rights rules are flushed out in court (how judges rule on cases) we will have to wait and see, but as it was said before, the majority of tenants are good, and you just need to ensure your screening process is sound. 

I know the urban crash rents by the room. they are a bnb set up.clients can be anyone at all that visit the city or anyone that needs a place to stay.consider you are having someone in your home, so you have to ensure its clean and presentable all the time.

If the park has it's own septic system you'll need to ensure there aren't any hidden issues which can be very, very costly. 

Hello fellow investors in Chicago area, do you have a recommendation on any attorney or title company who can help a private money lender to review the lending/mortgage doc to ensure the property is clean and the lender is registered as 1st position?

I may go that route, but wouldn't I have an option not to limit the amount I take out to ensure I do not incur the neg cash flow?

Whenever you are buying a property out of state you should do a few things to ensure it's as smooth as possible.Don't buy in the roughest neighborhood in the urban core.

For a buy and hold investor this is truly an awesome way to acquire properties, force equity, and see great returns all while you are learning and being shielded in a sense by working with a consultant to ensure the renovation is completed to acceptable standards!