(rents also peaked from $1900 to $2600 in 2 years)Sale Price  -             $360K - $370K in the area for same kind of units.            

Chicago has a fantastic real estate community, and there are plenty of networking opportunities.

One strategy is to pursue properties (in your preferred markets) that have been listed for sale for over 90 days (even longer is better).

He can spend the next few years-ish getting a finance degree through an online school while working part time, but he just got offered a full time position helping with sales for a local wholesale real estate company. 

I'm interested in evaluating RE investment opportunities in Dubai.

Additionally, property taxes may go up after a sale. 

Once you have your strategy/goals, begin underwriting as many opportunities as you see in that realm.

If selling properties, a 1031 exchange defers capital gains taxes by reinvesting proceeds into another investment property, while Opportunity Zone investments can defer or eliminate capital gains tax over time.Long-term rentals should be held in an LLC for liability protection and tax efficiency.

Until you sale or settle up.  

Is it mainly a sales pitch or is there good knowledge that you cannot find elsewhere?