There will be plenty of "on the job" learning experiences that you won't completely understand until you've encountered them even after reading about it every book and article.

Make sure you understand the condition of the property and if you will need to make any significant repairs or rehabs.Also understand the tenant situation. 

A lot of sellers just don't understand the term seller financing. 

I understand that there is minimum lot size to build a structure in Lee County / cities, so you would want to look into that as well, especially in Cape Coral as I heard that the lot sizes tend to be smaller there, and multiple lots would be needed to build a house there. 

Originally posted by @Josh Kundrat:Since it's in Chicago you might wanna avoid security deposits and opt instead for a non-refundable move in fee I don't understand this reply.

I've considered it but have not executed.In regards to the heloc if I understand things correctly you will not be able to take out a heloc on a investment property but simply a loc or a blanket/commercial loan depending on the financial institution you decide to approach with the situation.

Understanding where assets are in the life cycle will help you command more deals and better ROI.

If I understand correctly this property is one that you 1031d previously and now want to put into an entity with other members in exchange for membership interest.  

Appreciate that your humility in understanding that there is always something new to learn.

I think having access to the MLS would really help because from what I understand there are a lot of tools you can utilize like seeing average days on market, seeing comparable sales, and a lot more I'm sure.