Also don't see why you couldn't do both- work on real estate and training both in parallel to help boost savings.

My concern is that I won’t have time to book many short term rentals until after the stay and how that might delay boosting rankings,etc on Airbnb/Vrbo. 

Within the conversation for rates, there is another alternative that offers speed and may even boost your comps in the area.

There is often either friction between Board members, making real progress or change very difficult if not impossible, or a completely apathetic mentality, where most just go along, to get along, with whatever the Alpha Dog puts forth, with no real consideration as to what is actually in the best interest of the entire Membership for the long term.Often they do not take the time to learn about their own Governing Documents or Budget and Reserve Funding.

Nothing will boost you farther or faster than solid relationships. 

I'm looking at my first investment property and getting a mental block. 

Buying first property-- heck submitting your first offer-- can be a big mental step to overcome.

You want to keep long-term "good" tenants that have an ownership mentality, right?

Tenet B has said things like "seeing these mice have affected my mental health and I am not sure what to do" I am not sure if she is suggesting that she wants to move out, or something else. 

You should mentally evaluate the property as an investor and not just a guy that lives there for cheap.