As for STR, you're generally going to want to be looking for one of three markets: (1) Destination Markets -> Think Hawaii or Malibu or Aspen (2) Industrial Markets -> Think Austin, Greenville, Atlanta (places where tourists don't contribute to the better majority of all dollars spent or (3) Vacation Markets -> Areas with a good mix of tourists and long term residents and the vacation goers don't need to book their trip that much in advance. 

Sergey is also correct anchorage has been seeing a slight population decline over the last few years but with a thriving summer tourist community, the short-term rental market made a large boom.

The area is in close proximity to some tourists hotspots. 

These look like nice tourist towns and I would like to explore an short-term rental.Currently, I have several SFR rentals that are all long-term.

But any city that is a tourist economy is going to be preferable for STR, rather than a metro market that might change the regs next week.

Here is what I gathered from the investors or my own observations/ experience 1) owners don’t pay utilities, sales and tourist taxes, routine maintenance (almost every check out, a touch up paint is needed as guests leave wall marks with their luggage; just a basic example), inventory ( sheets, towels, furniture, and etc) 2) in long term, tenants cover lots of maintenance; so another saving. 3) in long term, occupancy rate is higher and more stable. 4) long term rental rates are high today. 5) townhouses or condos have to compete with the hotels, and Orlando has more of these than any other city probably in the world.

I’m looking to purchase an STR within driving distance of Madison and what I’ve discovered through my research is townships that, while they cannot outright ban TRH (tourist rooming houses), they subject them to a conditional use permit through the zoning office.  

What tool/website do you use to find out the volume of the guests/tourists for that area?

Theres allot going on for that area thats coming to keep prices on the rise and bringing in more tourist. 

While it's a strong tourist market, the City has also limited the number of permits so properties that come up for sale with an existing permit are snapped up quickly and command a higher price.