I thought the technology of the Model 3 would make me safer. And that's true, except that I found I don't so much like AP. (I still want a car that will let me sit in the back seat and close my eyes.) I thought that after 7 years it was time to move on to a more practical car and that I don't need two electric cars. But if I can make my Canada trip in the Model 3, then it's the Prius I no longer need.
On Maui the big advantage of the Roadster is the open top. But there's still the problem that it cannot haul anything, and if a couple comes to visit me I'd have to rent a car if we wanted to drive anywhere together. Even here at home, the Roadster needs another car to haul its tires to the tire place twice a year for switching between summer and winter tires. At least on Maui it would be summer tires all year around. (Though tires will probably cost twice as much there because of shipping.)
So I'll enjoy the Roadster for another year. If The Model 3 works out for Canada, I'll sell the Prius. If I end up only spending winters on Maui I'll keep the Roadster and the Model 3. If I end up moving to Maui I'll probably have to choose one or the other. In the mean time, it's going to be a PITA because the Prius needs to be plugged into a battery minder and I don't have space to plug in three cars. There's going to be some juggling of parking space.