Do you think this strategy gains strength if lets say... in five years interest rates are at 5.5 vs 7.5 now?  

I recommend you take some courses on underwriting that are geared towards passive investors.

There is no Passive investing.  

But have you gained anything? 

I'm struggling a bit on that comparing the passivity, appreciation, etc

The challenges in real estate teach you invaluable lessons that you might not gain otherwise.I also invest in Chicago, so I have a few thoughts in response to the questions you raised.

I think so many folks maybe are looking at these deals like its passive investing etc.

In that situation, I personally would not be investing in direct real estate at all.If I wanted exposure to a foreign real estate market, I would invest passively and hire a manager that has years more experience than I could ever hope to gain, and whose job is to supervise and watch everything and make sure that it goes well.Just my $0.02.And whatever you decide to do: good luck.

Although the study may increase the gain, the gain may be taxed at a much lower rate making it a beneficial investment.If a property is purchased with the intention to flip or own for a short period of time (less than 3 years), a cost segregation study may not be significant.SHOULD I GET A COST SEGREGATION STUDY BEFORE OR AFTER REHABBING MY PROPERTY?

Depending on the situation, it could still be worth it for SFHs especially if you have capital gains or other income you need to offset this year.