I currently live in Chicago and own a 2-flat. 

You know him better, so use your intuition to determine the best way to have this conversation.Silly question, and maybe I am just naive, but don't most contractors bake these admin/reimbursement costs into their total quote?

I have been using the flat type for years.

When I found deals they would partner with me and either buy the deal from me and pay me a flat fee, or we would partner on the deal and I would see it through till the end.

If the project only cashflows with interest only payments, that isn't a deal to me. there are going to be other costs involved such a cap ex and maintenance, so you will need to bake in a certain amount of expenses beyond jsut the mortgage payment too.

In that example, they would be exposed to section 1250 recapture at a flat rate of 25%.

An LLC for your 2 flats or duplexes, another for apartment buildings.

Get all the parties on a conference call.I tried, and believe it or not, title company flat out refused to join a conference call with the accounting firm.  

If you think PITI stays flat, that's naive--thinking it means you're property did not appreciate and net depreciated against inflation.

We offer flat rate Property Management.