@Arthur Wilson III if you are looking for a mentor I would highly recommend getting involved in/attending any real estate investor associations in your area or any BP meet ups, like you already mentioned.

In IL, we have attorneys involved on every deal.

I work with a great team who is in the top ten for the company and have been involved with RE for over 17 years. 

The 1031 involves timing and discipline. 

For example if you go into a house and it needs paint, new floors a kitchen and bath, do you price it out per square foot?

(especially if you're looking to reside in the property part-time) Short term rental by airbnb/vrbo is one possible solution to offset the cost, but you'd be faced with the tax in full and everything involved with property management would apply. 

Trying to become a lot more involved on Bigger Pockets as it seems to be the way to go these days when trying to connect globally.

What you are looking for is more B and C neighborhoods, Irving Park Avondale, Logan Square, West Town I would say are B neighborhoods etc.

I would definitely get the attorney involved in writing a letter, so that they see that you're serious. 

$70 a square is a great price especially if includes the land!