I wrote
my reply above almost two years ago, after less than a year of Tesla ownership, but I'd give the same advice today. In a Tesla, in the United States, and along major highways, there are enough Superchargers that you don't need to follow any route planning software's advice precisely; you can stop earlier (or sometimes later) than the route planner suggests. Route planners tend to optimize trips for the
car's needs, but in a Tesla, most people end up needing to stop for longer than the car does, so that opens a lot of room for altering the suggestions on the fly. (That said, some people like to do "canonball runs" with minimal stops, and my experience and suggestions don't apply to them.)
As to your specific questions, starting a trip at 100% will give you the most options as the trip progresses, but charging frequently to 100% is bad for the battery. I wouldn't worry about that for a road trip every few months, but if you go on road trips every other week, charging to a lower percentage is probably preferable. Lithium-ion battery health is best when it's kept in a middle range, as close to 50% as you can manage; but of course that defeats the purpose of having a battery in the first place. As with charging to 100%, I wouldn't worry about draining the battery very low or charging very high on occasional road trips. Tesla occasionally releases data on battery degradation, and third-party sites like
TeslaFi also track Tesla battery data. Both show modest battery declines over time -- typically a few percent in the first year of ownership and smaller amounts in subsequent years, with older cars having around 90% of original range for extended periods of their life. Although some owners do baby their batteries, many don't, and stories of Teslas with badly-degraded batteries are pretty rare. Overall and IMHO, concerns about battery degradation in Tesla (and in most EVs) are a bit overblown.