I would recommend tuning into Straight Up Chicago Investor Podcast and going to local meetups. 

i like your idea to stay local. 

I honestly wouldn't trust anyone else with my clients but him when it comes to that local market.

He gives realistic no fluff advice for those starting out and of course that's a huge part of BP audience not the guru's or the guys at are at the top already or say they are.. but real advice on how to work in a local market and do the things it takes to get there and how long it generally will take a person if they are dedicated extremely focused on the goal as Steve and his family were. 

I would consider the tenant's past, as well as the condition of the unit, my local market, and other factors.

First you have to face the local municipalities & will be extremely difficult to get the zoning approved. 

If the locals say it's rare then I would not worry.

A buddy of mine who invests out in Phoenix once had a client facing a similar timing mismatch on a rehab project.. they ended up working closely with a local credit union who was more open to interim valuations.

Mine was also out of state, in a town I’d never visited, and I relied heavily on videos from my agent.This sounds like a tough first deal, but it seems like you have some capital on the side, which will be useful as you face the upcoming challenges and learn from those expensive early mistakes.Regarding the subject of this post, “help me adjust my expectations,” I’d recommend assuming that; repairs will cost twice as much as you estimate, maintenance and vacancy rates will likely double from your initial projections, there’s a very real chance you may lose money on this deal.That said, there are ways to mitigate these risks by:- Keep asking questions here on BP and connecting with local experts- Stay proactive and communicative with your agent and property manager.And remember “Inspect what you expect.”Im not trying to discourage you but to help reset your expectations.

You could even try reaching out directly to local agents or small real estate firms.