Risk of being the 1, right?

I have several ideas.

They told me they only adjust every few months, it has been over 7 months since I made several requests.  

The management company replaced some of them, however there are still several other fees related to the theft that we are trying to get reimbursed for (they told us we would not be charged, they charged us anyways).

It sounds like you have an un-permitted unit, which is essentially always a risk since there has been no notice to the AHJ that it exists and they can therefore initiate a code case to have it removed in most cases.

We are starting to explore options for buying his shares to eliminate him as a risk and a roadblock but still have funds leftover for growth.

Diversify if you can with smaller amounts so risk is distributed. 

I began considering real estate after the 2008 market downturn, and started investing several years later.

I would definitely reach out to several brokerages within the area that could better facilitate as the middleman when Insurance Companies do reach out. 

@John Reagan Johnson hope you don't mind a PMC answering, but most of our clients hire us because:1) They live out of state and don't have time & expertise to remote manage2) They don't have the time to manage3) They don't feel they have the necessary expertise and/or don't want to risk learning as they go and making an expensive mistake.Go read Kiosaki's Cash Flow Quadrant book.