Relatively new to the Chicago area (summer 2016) after moving around a bit.

Related to the contractor, or any service provider, I think it is important to choose quality and reliability over price.   

Just willing to help, I love anything related with real estate, I wish to get involved asap, Thanks :) I live in Wesley Chapel, Fl but I can move easily all over the Tampa, Fl area.

Others have said that the only look-back to worry about is if the original 1031 exchange was between related parties (it wasn't). 

Do they have a lawyer involved... or is this info all related through a "conversation in the back yard."  

Doesn't necessarily have to be real estate related. 

Also, quite frankly, I don't really know what I want to do for a living and have been exploring some real estate related career paths (Loan Officer and Broker mainly but my eyes are WIDE open).

The FB analytics dashboard is also phenomenal, albeit a little creepy with how much info you have access to.If you're looking to promote some type of RE related business/service google adwords is great, but can be expensive.

He constantly watches who comes and goes in his landlords unit, watching their relatives coming, them cooking big dinners, and how many dinners a week.

If the property has been  well maintained (I know, this can be relative), usually $1k is enough to turnover (carpet cleaning, professional cleaning of the rest of the house).