The only real downside I can see is that it's now 4 rather than three members and one of those members is iffy anyway (or communication hasn't been great between you to date). 

Now they haven't paid July rent, won't apply for the state's rental assistance, and have stopped communicating. 

I would communicate to the tenant that you are getting an appraisal done, and provide them enough notice to prepare.

I have been communicating with several different agents in the area but primarily my targets that I have been sitting down and picking brains with recently have been either property managers or agents who are specifically involved in REI.

It really depends on how you will be using the software; if it will be your management "hub" for all data and all communications vs more of an accounting software.

I think the best ways to protect yourself are probably an umbrella policy, your lease contract, clear communication with tenants, and quickly responding to emergencies that may lead to bigger issues.

The good ones get a premium, the rest are bad at communicating, have sub-par skills, or simply don't show up.

Communication is key for me and keeping an open dialogue with my roomates/friends.

Communicated some recommended suggestions to moderators.

Get clear on what your goals and expectations are and communicate them up front.