And if your mom does not have a house for herself she owns  (ie. if she currently Rents )- then that would not be a bad place to start in my opinion with some of the money she might gain from selling the house.  

I was happy to gain access to my funds, but it did not make up for my wasted time (about 3 wks) and their unacceptable treatment initially.

Slow down, get these 4 units stabilized, get some traction, and wait.

Often newer investors want things to cashflow and cover their mortgage, but the riches in real estate (in my opinion) are in GAINING EXPERIENCE......so consider just finding a property where if you were to rent in the same neighbhorhood your mortgage is less than that amount (less rental income as well) - that to me is a win period...Are you looking at any specific areas of chicago?

How is the capital gain calculated if I live in the larger unit for 2 yrs? 

We are largely looking to gain some tax advantages through investment properties to help offset the W-2 income.

All of our assets have significant cashflow, large built in capital gains, great LTV position, Loans are at 7 year, 10 year and 20 year balloon terms.  

What happens if one of you decides to buy a personal home and need the credit to qualify for a new loan so needs to sell this one to make it happen, but the other partner not ready to sell yet, or doesn't want the capital gains. 

I've been wholesaling for over 8 years and I promise you, there is more knowledge to be gained by getting started and learning from real world, hands on experience than from paying $2,000 - $15,000 to some guru from Youtube.

These properties are the ones that show the impressive 3x and greater price gains.