I'd really like it if we could just fly to it, preferably, with a seamless transition.
This is unlikely, since we would have to load an entire map, so it would most likely be one or both of these options:
1: Select a start location (North Yankton or Los Santos)
2: Fly in a certain direction and once you get to a certain point, a screen pops up saying "You are too far from the action. Would you like to travel to North Yankton or turn around?" There would be a button prompt with 3 options:
X: Yes
Square: Turn around
O: Cancel (And drop out of the sky or sink in your boat)
EDIT: Another idea. If this is a paid DLC, and you have a friend in your vehicle that didn't pay for N.Y., what happens when you teleport to North Yankton? Do they fall out of your vehicle? Do they teleport with you? This has me thinking this will point to the "Select a starting location" option above.