Finding a local agent is helpful for sure but with today's technology, a broker who specializes in Chicago should be able to work nearly every neighborhood and get help from some colleagues if they are not super familiar with a certain area. 

Spend some more time educating yourself and looking for a deal that cash-flows better.

@Dave Foster's suggestion of a 1031 exchange might is worthwhile to consider - even if you look for property to rent out today that you may eventually move into down the road.

its kind of nice to see things leveling off .. so you just need to back into your deals at todays prices.. 

You need to incentivize them to mentor you or partner with you, either you work pro bono for them or bring something to the table of value.To your comment about "shady" or dishonest, I would encourage to you be as honest and forthcoming as possible, I don't know about you but I got into real estate because I wanted to do something meaningful, profitable for my family's benefit, I wanted to benefit from my level of effort rather than giving it to someone else, and most of all I wanted to make the world a better place by improving whatever it is I am working on; I want to be able to lay my head on the pillow at night knowing I did everything I could today to move forward in a positive direction and did so with integrity in order to prevent any form of regret. 

That could be a great way to find and stay engaged with local investors and opportunities. http://www.biggerpockets.com/alertsYou can also search for other investors in that area and follow their journey on Bigger Pockets here: https://www.biggerpockets.com/search/usersAlso, be sure to get plugged into the podcast - it's been a wealth of education and a huge confidence builder as me and my husband have pursued REI and built our portfolio.

Much better to get him out asap versus waiting 2-3 months and then stlll having to go through the process.CAll today!! 

That could be a great way to find and stay engaged with local investors and opportunities. http://www.biggerpockets.com/alertsYou can also search for other investors in that area and follow their journey on Bigger Pockets here: https://www.biggerpockets.com/search/usersFinally, if you haven't already plugged into the Bigger Pockets podcast, I can't recommend it highly enough - it's been a wealth of education and a huge confidence builder as me and my husband have pursued REI and built our portfolio.Best of luck to you and look forward to following your journey!

Hello BP, I am currently an educator from NYC.

Today is my 45th day.