Hopefully your lease says something about utility bills being owed by the tenant - you should be able to make those "rents" by posting to the ledger.

I planned to use Avail for tenant screening, lease signing and rent payment.

I like Welcome Home Milwaukee, Citywide Rentals & MKE Leasing myself. 

Then you get a copy of all leases and read them all.

And lastly, make sure the property management company has experience leasing and managing Section 8 properties, since there is a lot paperwork and processes, and I've seen experienced property management companies who do this stuff all the time, screw up on multiple Section 8 leases to where the tenant's packet expired because they were so incompetent.  

Any items billed to the tenant under my lease as "payable as rent".

With proximity to a hospital and a university, there's potential to attract both traveling professionals (for MTR) and students or faculty for long-term leases.

Every tenant would have there own lease stating the rules and responsibilities for BOTH parties.

You would need a "Post Occupancy Addendum" or a month-to-month lease.

I had to build fences along my driveway accessing a drive under garage, because the retaining wall was more than 30" tall (standard building code item) but these properties were built in the 40s/50s and never had a fence there until I rented Section 8 and they required it.From a tenant perspective, I never had any of the issues James notes.