Therefore, I ended going with the Gold plan which was about 20k, putting most of my savings towards this buy in.

This wild ride underscores the power of relentless follow-up and the hidden gold in every lead.

A recent guest?

Ensuring the safety and security of my guests and property is of utmost importance to me.

Is it wrong for me to believe that going unrepresented, I may not be missing out on much especially since the agents themselves did not represent their interests other than wanting status quo.

See https://www.gridstatus.io/live for the real-time grid monitoring, status, and rates. 

I particularly resonate with the idea of 'always be analyzing'—so crucial to stay flexible and adapt to changing markets.Your point on opportunity cost is gold.

It offers coverage for guests even when they are away from the house.

Bigger Pockets Podcast #82 guest 

The key factor is ensuring the property qualifies for favorable tax treatment by adhering to IRS rules regarding short-term rentals and material participation.For the 7-day rule, the IRS requires that:The average guest stay must be seven days or less for the property to qualify as a short-term rental.If the average stay is 30 days or less, you must provide substantial services similar to what hotels offer, such as daily cleaning or concierge services.Regarding material participation, to further classify the income as non-passive, you must meet one of the following criteria:You spend more than 500 hours actively managing the rental in a year.You manage the business yourself and spend at least 100 hours, with your involvement exceeding that of any other person involved in the rental.Please note there are actually 7 ways to qualify, the above two are the most common.