I have no idea who I should reach out to for help, and I just do not understand how this person no longer responds to emails or returns phone calls.I hope someone can provide some guidance. 

Learnt lesson not to fully depend on property manager and should have made decision faster by reducing rent .

As for your ques if to wait, well, it depends on the market, in some parts of the country prices are still going up, slower, but still going up, other parts the prices are coming down, you know that area, what is happening there? 

All of this really depends on your goals and timeline though too.

For a smaller piece like that, not sure how creative you can get, but it all depends on what it's zoning is, access, proximity to other things, etc.  

This way the wider outside lip contacts the entirety of the drywall while the wings are being deployed and tightened in place.Is there a way to pull the already wired, "old work" electrical boxes through the drywall cutouts from the inside out while not making the holes so big that the wider, outside lips of the electrical boxes can't properly provide contact to the drywall so it can be tightened via the screwed wings?

Depends on their health and any desire they may have to simplify.

They are very nice and can be helpful providing you what you can and cannot build on your property (Set back, height restrictions, front look etc).

I think it really depends the style and setup.

However, I believe multi family provides the best ROI and is the best way to scale.