I don’t think the Airbnb market here is very popular but it seems like there would be enough people that visit the park that would make it worth it.

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.

If there is time and money available that is the opportunity to make a choice, but that usually involves INCREMENTAL upgrades like painting a room or replacing the flooring in a room or 2. 

Those would be my choices if I exit Indianapolis. 

Making the choice to partner was a no-brainer for me because she likes to do the things that I don’t like to do and vice versa.

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

https://www.biggerpockets.com/blog/short-term-rental-loans-a...DSCR Loans: Terms to Know When Working With These Popular Rental Loanhttps://www.biggerpockets.com/blog/dscr-loans-terms-to-knowWhat’s Next For DSCR Loans?

On listing side, again was fully compliant but now just adding 1 more disclosure and agreement to it all drawing it all out in "crayola" as seller defines THERE choice, that it is there choice, and most importantly the extra clarity on dual agency because THAT is biggest impact I see coming, a whole lot MORE dual agency. 

Hi Daniel, as a Miami-based Realtor who works with investors on new/pre-construction purchases, as far as location is concerned, I agree with your choices of Miami Beach and Downtown Miami.  

They are a poor choice in most situations.