Few thoughts:
1. Be prepared that road-tripping a Tesla (or any EV) needs a little different mindset compared to road-tripping an ICE car.
a) Special note for general aviation pilots: Think of doing a cross-country flight in a GA aircraft.
2. Drive on the "bottom" part of the battery for more efficient charging. Charge enough to make your next charging stop, then move on.
3. But don't be afraid to "fill 'er up" if you really need the range or you're heading into a "charging desert".
4. Be flexible in your plans, particularly if you're traveling on holiday weekends (or other busy times), in bad weather, or if you have to go off the Supercharger networks.
5. Hotel charging is great (assuming it works, which is usually but not always the case). Try to plug in when you arrive, rather than before you leave.
6. Bring all your charging equipment with you (e.g. mobile connector, J1772/CCS/CHAdeMO adapter etc.). I'm not saying you need to buy anything in particular, but just load up whatever you have...those adapters won't do any good sitting at home in your garage.
7. You can use the Tesla trip planner feature in the nav system, but sanity check whatever it tells you. Trust but verify.
a) Personally I plot my charging stops out manually and just use the car nav to get me to the next charger, but I don't recommend that approach for everybody.
8. Bring some windshield cleaning supplies if you have them, you won't be using gas stations as much.
Hrm. I really ought to make a one-pager out of these.
Bruce.