Thank you for taking your time to spell it out, taken to heart!          

I was slated to lose $24,000 on an expected breakeven BRRRR.After a small heart attack, I reached out to a few RE professionals in the area and the general response was "That sucks!"

I have looked into a few markets but I now have my heart set on Camden, NJ.

Mentors teach from the heart!  

Chicago as most have seen and I have personally experienced is a VERY tough place to do business and you need huge margins to allow for profitability given the challenges of permitting and construction in the areas these assets are located... its not for the feint of heart that's for sure. and if a lender ends up owning these its a wipe out generally  LOL... ask me how I know.

In Pittsburgh they developed the polio vaccine, heart transplants and 7 organ transplants;  they didn't do that at the Bessemer furnace.I've said it countless times on Bigger Pockets and other places that "Tax Sales are the most hazardous method of buying real estate." 

These people are busy, and their time is money, so it needs to be worth it for them to help you out - most people aren't just going to do it out of the kindness of their hearts because they just don't have the time to spare (and they get asked to be mentors all the time).It probably makes sense to work with someone who already has assets in the area, since they will be familiar with rents, comps, etc. and can best advise you.

Don't lose heart!

Had I done it myself I could have pursued the sub-2 route, however, my goal was to have multiple projects ongoing at once and leveraging OPM was still at the heart of my strategy.

If you are weak of heart and think about it longer the bleeding continues.