I’ll lay out my situation, goal and how I think I’d like to achieve that goal.

The best way is to show your inner network your business plan for the building and how it'll benefit them and how you plan to achieve success

It feels great to have achieved this!

If your current property has achieved max value and it is just following the market trends, I would sell IMO. 

You'll most likely see land values chase that attention in the future but to me the getting is good to buy rentals up there even if you just buy off MLS and do conventional in decent areas, CF and Appreciation can be achieved relatively easily if you have even half-way decent resouces.

So, you need to force the issue by selling 10% at what ever price you can achieve before more conventional lenders.

I am interested to hear what everyone thinks about how you should analyze when the optimal time (financially) is to sell a rental property. 

If it takes a massive number of units to achieve better results, that would be the way to go. 

Background; I am interested to learn if I am going about my rental business the right way, or if there are ways I can optimize?

Being flexible is a necessity along with setting dates for taking action and achieving goals..