So I've got the original TSW and the Long Island dlc, does anyone know if I upgrade to TSW 2020 will my dlc work still, and what, if any perks do I get for upgrading?
Is your original TSW on disc or digital? The base software should update for free to TSW 2020 and your DLC will be unaffected. If you buy the 2020 digital version, you'll be in the same position, but will gain whichever of the new bundle DLC you don't already own.