I have it narrowed down to two agents, one has more general experience in the area and are part of a large organization.

Just make sure the other two assets can still cash flow with the debt you put on them.I have an 10 unit commercial property that is basically cash flow neutral because of large Capex expenses that come up every year.

I would both buy a property to get your feet wet and at the same time make a plan to scale.  

Quote from @Jonathan Grzeszczyk: David Greene has a series (Sold, Skilled, Scale) that teaches agents how to run their business like a business.

I know you mentioned taking time to relax, do you plan to further scale or do something different outside real estate?

Large tree in back is dead .

The building's Property Manager is sympathetic to the owners at large, but says they can’t do anything until instructed by the Board, and they indicated the building’s lawyers would only respond to Board members.

A young population plus a growing industry makes for good long term investments, but unless you are really scaling the cashflow can be hit or miss. 

Buying a large new build home can also work well as a house hack as you can charge a premium rent, and generally most bedrooms built now a days have en suites (at least in my market).  

I have a team and large network of wholesalers, contractors, property managers etc.