This is true regardless of how long you have owned a vacation rental. 

I used to own a large SFR management company I sold to Evernest in 2019 and I manage a Kroger SC and a set of retail condo suites for a client now but it isn't my thing. 

I've consistently written about the forces of nature and her current and future effects on the real estate market (even while often being ridiculed and politicized on this very site for it) regardless: I personally moved and invested in coastal Oregon in 2018 from Venice Beach Los Angeles partly as a result of the trajectory of climate and have assisted several clients that specifically purchased on the Oregon Coast for their own 'climate havens,' investment and future retirement homes. 

If I were you and you need to meet the requirement of working under a Broker, just make sure your agreement with the broker allows you to take all your properties with you once you leave, obtain your brokers license and start your own brokerageI would also start looking at software systems and joining the National Association of Residential Property Managers.

Paying more to guarantee getting the product versus jumping through hoops (short sale) or possibility of now owning it at all (auction).I'm only asking questions to understand!

The community has its own internal lake, which connects to Lake Toho, via a boat lift owned by the community club.

It’s a common practice and I’ve never had any opposition to this provision.If you don’t have an operating company, you could get into contract in your own name and then assign it.  

I've also heard of requirements to own for at least one year before you can use the home as a STR.Hawaii is a leftist state that doesn't protect private property rights.

Greatest financial pitfall when owning a rental property is vacancy time.

And yes that poster has a trail of his own.