I can't speak to the Denver market since I'm in DFW, and obviously can't speak to the specifics of your building since there are so many varying factors. 

Given these numbers and solely financially speaking, should I sell or hold the property?

“I cannot speak for ORES.

But, that is not always the right answer and you should speak with someone familiar with your personal situation to get advice specific to you.

We use a separate property management software for everything else, so I can't speak to the rent collection features.

I'd love to speak with any property managers who run properties in the Villages, Florida.

It also depends on market conditions and availability of cash in the market, both of which will create more or less "meat" so to speak in the deal.

Quote from @DeAnna McKillop-Lopez: I have been hearing a lot of people speaking about putting your holding LLC into an irrevocable trust.

This is actually one of the main reasons many agents and investors may not like them generally speaking (they are often not serious professionals with a proven track record of success, the vast majority are struggling to find their first deal and are time-wasters to interact with).   

I can't speak to the quality of his course though as I've never taken it.