Solution to #2 – there should be a clause in the management contract that provides a threshold where any work above a certain amount requires owner approval (emergencies are handled separately).

Rents for $1750Mortgage and Escrow: $550Utilities: $450(high end)Property Management: $105Estimated Profit: $645Utilities Note: the gas and electric are not separate so its included in the rent.Would it be smart to hire the property management company right away or wait until we have five or more properties?

It's good that you've built that into your budget, but if this is a 4-plex then check whether the utilities are metered separately or together. 

If I do need a separate roommate agreement, do you treat roommate just like you would tenants? 

Action is what separates people who talk about real estate investing and those who are real estate investors.

A Renovation Builders risk policy (if it does not include Liability coverage we do a separate Liability policy)2.

Would that be on a separate JV agreement where I would write that?

I've never been a fan of non-separated utilities, and I worry if RUBS might have some headwinds in a place like IL. 

There are probably some uptight agents out there that would hold you to that agreement but if not's not working out it's usually beneficial for both parties to go separate ways at that point anyway. 

The Triplex is in pretty rough shape, there are two units which are stacked (upstairs and downstairs) as well as a separate unit.