Section 8 is awesome. The process is pretty easy actually, it just takes a while. I've done it twice so far.
When we finish reno, we list on GoSection8.com and Craigslist and set up a couple of open houses, and we usually find a tenant at that open house.
From there you fill out the application packet for them, submit it to RRHA who either approves the rent amount or asks you to lower it, and then they tell you what the voucher covers and the tenant must cover.
Next, they schedule an inspection of basic safety. It's not very difficult to meet the standards and they give you a chance to reinspect it once if it fails. BUT ONLY ONCE.
Once inspection is passed, you just sign the regular lease with the HABS contract attachment that represents several guarantees to the RRHA (ie: you won't sell it within a year, raise rents within a year, etc.).
I'd say the process from app to move in is about a month if you and your tenant are on top of your game.
Tip: Always hand deliver the paperwork and get a receipt. They will mail the paperwork to you, but you should always hand-deliver stuff to RRHA to speed up the process.
We currently rent section 8 in 2322 by the racetrack. Our 2/1 gets $830/month, our 3/2 gets $900/month, but that's because that was my first time doing Section 8 and was trying to rent it at market, rather than what section 8 would pay which is usually above market in Class C neighborhoods. Our 3/2 could probably be getting $1,000 to $1,100 had we done it right.
We are currently renovating 2 more houses (South side) and will rent those Section 8 for the higher rents.
One thing to keep in mind is that a tenant gets evicted, they lose their voucher. That voucher is like gold to those tenants, so you'd be surprised how well they keep the property up. You just have to treat them as first class tenants and not like second class citizens as I think many Section 8 landlords might do.