The PM charges me 13% flat rate (so not lease fee no renewal fee no upcharge on services etc etc) which works out for us.  

It's too high demand, and the potential appreciation is baked in to most of the homes we are looking at - that don't require a near complete gut/reno.

I have yet to be flat out denied nor have I been required to address anything more than what is visible (usually attics and/or basements).

This will be your local flat fee eviction attorney and your go-to guy in case you need an eviction.Step 4 is setting up your rental criteria and a  process for screening and evaluating tenants.  99% of potential tenant problems will be prevented by proper screening.Step 5 is taking prompt action when managing your properties and you notice minor lease violations, late rent, etc. 

For example in 2003-2007 rents were flat and down in some areas as everyone was buying a home.

I am no expert but I would flat out refuse under those terms.

Im closing on a 2 flat in chicago in a few weeks and just found out one of the tenant is section 8.

That 5K could be eaten up quickly by repairs that were not visible up front, and then there is still the fact that there will be closing costs too that will consume that 5K (even flat fee listing on the resale with a 2.5% commission to buyer's agent will take more than 3K alone).Maybe this can work as a "subject to", but that is another topic - and it might not be a good candidate for that approach because you still have that big rehab number.

Would you do 2 level townhouses/row houses or flats with one family living above the other.

A factor that greatly increases roof costs is composition or flat roofs.