I always remember that rockstars know rockstars, so find someone who is a mover and shaker - likely a meetup host - and then ask them who they know.The people doing 100 flips are super busy, so I've also found the best person to find is someone who is a step or two ahead of me...so maybe for you, that is someone doing 2-3 flips a year. 

Chicago has such a great investing community compared to most places in the US I have visited!

Condition we want is move-in ready, and ideally no more than 10yrs but go ahead and put that fence at 15. 

I would go ahead and set one up.

So, I'd like to get ahead of the game and start working up a plan and a strong argument for it which I can use when the time comes. 

If you do not have an FHA mortgage then go ahead and apply for one on the investment property. 

That may not apply to you, as a financial professional, but I thought I would share the story.Obiously you could re-lever your portfolio to bring the ROE back up, but then you have to place those borrowed funds somewhere that nets a high enough return that the portfolio is ahead, given the drag of the interest and any transaction fees.    

Always good to look at the setup and look at the meters while you're visiting the property.

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.

However, all of the investors really like the property and the care takers and they like to visit and bring family and friends to the property.