I would also suggest going the section 8 route on a few of the units in what I would consider more challenging neighborhoods.On maintenance bids being high, negotiate everything.

You haven't even asked about your BIGGEST challenge - finding "trustworthy" contractors.- Most contractors will cut corners, or worse, once they figure out they won't be watched closely:( Your job will also go to the bottom of their priority list.Monitoring progress is relatively easy: hire that same inspector to go by weekly or before any payments to take a VIDEO of:1) What was done2) Quality of workmanshipOne other thing you didn't ask about, payments to contractors.- They all want 50% down or as much as they can squeeze out of you. 

Realize the competitive market makes it a challenging market for beginners. 

Challenges?

Challenges?

So I'm curious whether anyone plays it, or whether the consensus is the Real World provides Challenges enough?

Tenant screening is challenging and you have to have the right process in place to make sure you choose wisely.The main thing as many said, this shows a red flag on the amount.

That said, tenants are people facing their own challenges.

Are you finding the funding process smooth, or do you run into challenges?

Years ago, a friend of mine took on a similar challenge in an older neighborhood near Chicago..he opened up the top floor to create a master suite that felt less like a converted attic and more like a boutique hotel room.