But if it is turnkey, I am assuming you will probably not be ahead on cash flow from your current property (and likely less).But I want to reiterate, if you say you are an investor and your focus is scale and number of doors, you are measuring the wrong metric.  

As the comment above stated you'll have to find your plans/strategy but I don't think it'll be a bad decision you may be ahead of the curve. 

Therefore, I'd figure out how low my occupancy and rental rate can get so that I at the very least break even.If you want to get ahead of the competition, you might want to try to get something special.

Traditionally insurance companies collected premiums and invested in the stock market or other vehicles to increase their income.

If you are replacing a rent payment with this then 100% yes bc you will come out ahead.

Then go ahead and handle the listing and transaction yourself. 

I'm also of the mind that if your vacation rental is already ahead of the competition, do you absolutely need to invest in more amenities?

In order to do this, you want to make sure your loan to ARV on your initial bridge loan, or loan to costs if using cash, are low enough for you to come out ahead on the refinance.

I know they didn't make appreciation on the note, that was a rhetoric response to another responder who didn't see the difference between the two investment vehicles.

Just a heads up!