I highly suggest getting to some local meetup groups...here is BPs list:  https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a full list of the chicago meetups that I can share with you too if that'd be helpful.

I don't use Stessa and never have so I don't know what's going on, but I suggested they take a look at Baselane, which is what I use.

Being out of state, I would suggest vetting your "team", meaning find an investor realtor, lender/s (hard $ / long term), property manager, contractors, etc.

I'm curious as to whether others have walked this mile and whether you have any suggestions on how I can accomplish this. 

First off I took the realtors suggestion and listed with the property management company he promoted to me.

They might have suggestions or updates that could help with this specific issue.

Any suggestions on what to update/populate in our "rules" section to help us make this clearer? 

Suggestions on learning more about contract for deed?

From there, I would like to consider a 1031 exchange in the future to acquire more units.My current property management company suggested that they could handle a mid sized apartment building but I would absolutely not consider them for it as I believe they have overextended themselves and communication is lacking.

I will start work with EY as an auditor in the fall and have recently begun studying for the CPA exam.