Here. Everything you could want to know about planning road tripping:
How to save a lot of time on long trips
As far as the charging before leaving, I take the method of "care a little about not using 100% but not worrying much". I'll put the charge limit slider in the mid 90's % for the overnight charge. Then, when I wake up the next morning, I grab my phone and move the slider up to 100% to get it going again while I'm showering and getting ready. It'll get to about 97 or 98% or something by the time I'm ready to leave, and that's close enough but didn't leave it full for any length of time--good compromise.
And as for planning, I don't like planning much, so if the route I'm going is on Supercharger covered highways, I don't bother with making any lists or charts of stops and charging amounts; it just doesn't matter. (To get a quick look at whether it's covered, I use
www.supercharge.info) I did a 5,000+ mile trip across the country and back last year in 11 days, and I didn't even have the cities picked out yet of where I was stopping. I would just get up the next day, see about how far I wanted to go, like 500-600ish miles, and then book an AirBNB in that city that was about that distance with a Supercharger in it. Worked great.
But option #2 is if I have to go somewhere off the Supercharger covered interstates, or have to cross a large gap between Superchargers, then you do want to have a plan for that. I'll use
www.evtripplanner.com, but some others prefer
www.abetterrouteplanner.com. You can put in a route and it will plot energy use based on which model of car, elevation along the route, heating or air conditioning use versus outside temperature, speed ratio versus average traffic speed, etc. That way I can figure out if I need some charging in between those Superchargers and how much. Then it's
www.plugshare.com to find a spot there to use for charging that I can match with a meal stop.
And that's about as complicated as I get.