There may be some seasoning period for the change to take. 

Then I got a notice from the city forcing me to repaint the entire house during high season. 

Then when it has "seasoned" (usually 6 months to a year) and the bank will loan on appraised value, you refinance it. 

But over time we would expect prices in certain areas to reset to level out the premium of STRs relative to LTRs to reflect actual differences in management intensity, seasonality, and higher level of service needed for STRs and not simply the easy $$ arbitrage: "who knew there's people who will shell out $250 a night 20 nights a month for this place when i was only getting $1000 a month with this LTR?" 

I'm guessing season is pretty short, so would have to make pretty quick money to balance rest of the year.What does investment market in your area look like?

So from what I understand, with most lenders there is a 6 months cash out seasoning period.

Some lenders don't have any seasoning period for a refinance.

Since it is Halloween season I look for decorations in the area and well maintained yards with little to no leaves.

Hope you’re having a good holiday season.

That said, the cost of these units, as you noted, are affordable and surprisingly, prices have been going up even though we're going into the off season.