I lived in one unit for 2 years rented out the other 3 then moved on to another 4 unit and did it a second time.

Jason - I may be able to work out some kind of arrangement with my father as a partner.

If you try to get a seller financed second mortgage you may have to call around to a bunch of local banks and credit unions.

Hey Eric, I'm not sure about any meetups in the SW suburbs, but there is a couple that I know of in the Downers Grove / Lisle area if you're willing to make the trek: DuPage County Real Estate InvestorsLifetime Cashflow w Multifamily Real Estate Chicago MeetupI have not yet attended the second one I listed.

I second the suggestions made by others.

My fiancé is about to graduate law school and we will finally have a second income.

Probably your cost would be around 750-900 for the first one and 400-500 for the second one totaling 1100-1400 for total transaction. 

Second and third deals contracts signed and pending -- So excited - but wait... they want full executive summary and business plans with 3 year projections...

Second think of the 1031 as a carry forward of your basis. 

An option to get you into your first investment faster is  for you both to get a second (and maybe a third) stream of income.