Wow -- great to hear Tesla is being proactive about looking for ways to open up eastern Canada. I assume you're familiar with their subsidized HPWC program for hotels...
Destination Charging
I'd suggest J1772 over Tesla, but not necessarily the 100A versions, at least not for Grandfalls-Windsor. Only some Teslas can take advantage of that today, and it means an awkward amount of time waiting, ~5 hours, to continue your trip. My experience is there are just a few kinds of convenient charging stops:
1) Parking at an airport and flying somewhere for a few days, in which case 120V is just fine.
2) Staying overnight, in which case a 10kW J1772 is perfect. It's especially useful when hotels have more than one J1772.
3) Visiting a museum, or somewhere with hiking (like south end of Confederation bridge), where a 20kW J1772 would be useful.
4) Stopping for bathroom, coffee, lunch or dinner. This is Supercharger territory.
With Grandfalls-Windsor right in the middle as your primary recharging stop you're looking for a full charge, so at least in my case I'd plan to stay overnight. I think hotels have an incentive to make sure their chargers require an overnight stay for full effect -- that's a big deal when it comes to justifying their installation. If the costs were similar, a hotel would much rather install a pair of 10kW chargers than a single 20kW charger.
If you do come up with a plan please let me know. I'd be happy to contribute.