We are looking to purchase a property in the Hilton Head Island area to use both as a winter residence and STR for spring/summer/fall.

George Island.

I own and operate 3 STR’s in San Antonio and 1 in Marco Island Florida. 

I am currently living and working in Vancouver Island but Calgary has always been the city that I have aspired to invest in.

I have a beach house in Destin and a 2 BR condo in FWB (Okaloosa Island), and they both perform exceptionally well. 

Mostly that is land value, but it does give you a reference point.  

I’m in Marco Island.

We also attend the CFRI meetings on Merritt Island, when we've got the chance.  

Their 6 load balanced internet connection is rivaled by none on the Island and is therefore a magnet to all digital nomads.

I've looked for a bit but not too in-depth but I know properties out here are ridiculously expensive.I don't mind going to the surrounding areas (NJ or NY state) but I would like it to be accessible to manhattan via Train and a drivable distance.my question is, does anyone have any experience with buying properties in NJ, upstate, Long Island, even maybe eastern PA (big maybe). looking for a good ROI and somewhere not too far from the Boroughs.