On the site I search on the new listings are first so it only takes me about 7 minutes to cruise through about 12 neighborhoods.

Well, let's see, there is about 14,527 destinations to choose from, and about 47,398 opinions as to what is smart or dumb....

Ideally, I would like to buy in the Catskills since it’s close by, a popular year round destination from the city and has a history of vacation rentals but I know there’s more and more talks of regulations so I am open to other areas and would love to hear your thoughts/experience on the area.Would love to connect with anyone who has interest in the area and the short term world as well as agents familiar with STR who could help us in our search.

It's in a popular year-round tourist destination with a shortage of hotels and heavy restrictions on STRs. 

There's no employers in the area as it's just a vacation destination.

@Josef Bryan GersterI would continue to think hard on what else you can do to make the place a destination in and of itself.

If it was a primary residence, there are conventional low LTV's, and as a popular second home destination,10-15% down payments for a SFR is common for well qualified buyers.

We believe it will always be saturated, as long as Disney and Universal are popular destinations in the area, though.

Because any great vacation destination will provide you with opportunities to create a profitable STR scenario. 

@Ashley Campbell we have seen some tremendous success with STRs, specifically in the unique destination type of properties.