@Dan Geffen moved down there and knows the area well if you want to connect with a local investor.

We are out of state and have local property managers.

My PM quotes me and does the work on my buys to get them rent-ready and then manages them and I'm local but they do the same for many out of state investors as do many Property managers in Milwaukee such as Citywide Rentals, Welcome Home Milwaukee or MKE Leasing. 

Contractor – This is one I really need help from the bigger pockets community in the local area. 

I would suggest going to the find a lender tab here on bigger pockets to find a local lender who has the same products. 

There are also some locally I think through the AAR, I would reach out to them but if not I am happy to help!

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

We worked with a lawyer over there who is a US ex-pat who created and registered a local LLC for us, which owns our properties.

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.

@Jason Khoury I purchased my current residence, a duplex, from a local non-profit about 5 years ago.