A funny anecdote within the spirit of the popular aphorism, that “less is more”: It might seem counter intuitive as a host that sees a larger number believing it could equal more (income) or as a guest to think (less money per person), but both are likely agree that just because 2 people can fit on a moped, (hell ya) it doesn’t make for a comfortable ride at twice the gas 

The property is on a river with river access in a very popular short term rental destination.

I think you have valid points to backup the popularity.

Contrary to popular opinion, Zillow isn't all that there is to the market. 

One thing I do know about is the baseball field is really popular for big tournaments and having teams stay at a house vs hotels make a lot of sense but that seems seasonal.

See, back in the day when WE (notice the WE, not them or others) made the terms "cash buyer" popularly known, it was MORE a reference to our TERMS than our payment action.

When he wrote Rich Dad, Poor Dad it was also popular at the time to denigrate traditional college because we were right in the dot com boom, where a certification to write html paid more than a college degree. 

If I wanted to STR under these rules I would be Miss Popularity getting on the Board and giving out candy.

I am selling one of our STRs in a popular downtown area.

I suppose the easy answer is "until I run out of money" or "until the market gets better" but let's suppose there is no "better", but instead a market shift (i.e. oversaturation, market loses popularity, etc) or you're unwilling to actually run out of money - what then?