I disagree with everyone. I’ve been doing this for six years, first with Model S 60 and now with Model 3 LR. Charge to 100% at home before you leave (completing the charge that morning, so it’s not sitting at 100% for hours). There’s absolutely no reason to leave on a trip with anything less than a full battery. That’s what the 100% is for.
Regarding supercharging, let your activities be your guide. If you’re eating lunch, let the car keep charging until you’re ready to leave. That may mean 100% some stops. On the other hand, if it’s just a bathroom stop and you’re waiting for the car rather than the other way around, leave as soon as you have the buffer you need to get to your next stop. It might be just a 60 or 70% charge, but don’t take the time to keep charging if you’re planning on eating at the next supercharger and the car will have all the time it needs to charge more.
I just completed a 3300 mile round trip Austin- Philadelphia and I was amazed how fast supercharging is now at 145 kW. Rarely did I have to wait for the car, it was usually ready to leave before I was. We usually needed one short and one long supercharging stop per day, and were able to start each day at 100% by staying at hotels with destination charging.
And you don’t need to use any 3rd party apps. The car navigation works just fine. My suggestion would be instead of inputting your final destination at the start of the day, input the supercharger stop where you plan to eat (the longer stop) as your destination. From there enter your final destination.