I am fairly new to the Chicago RE scene though, do you know of other neighborhoods that have affordable turn key multi unit properties that are likely to rent and generate cash flow?

you should encoursage him to get in the industry then.. get a RE license and go make some dough its a lifelong career.. wholesaling at best is a flash in the pan.. great sales folks can make a killing brokering real estate in a high value market like NYC... many make 500 to 2 mil a year easy.

My name is Daniel and I'm new to RE.  

He is very familiar with 1031 exchange rules and works exclusively with RE clients.

For the most part I find decent information here.I do also suggest that there is literally no replacement for getting out and networking IN PERSON at RE Clubs.

VeronicaPS, I have posted this EXACT discussion on the REHAB category if you by chance see it again..

Are short sales less attractive since end of 2014, since now banks can go after deficiency or 1099 the owner?

I am reading and listening to podcasts that discuss the benefits of smaller, community lenders.  

I have a good tenant, but they have discussed moving in the future.

Aside from simple diversification, I'm excited about the other positives about the RE asset class specifically, and I'm just soaking up information, looking to learn and network with people in general here on BP and specifically here in the SD market.