Welcome to long distance electric travel.
When we first started we over planned, however if you are off major interstates or where there are not Super chargers you need to plan. When we first purchased our car and traveled west we needed to plan and to slow down... Today not an issue many more Super chargers
Supercharging is great in general as the threads state you will not generally run into crowded superchargers but is does happen. Anyone who has come through Bethesda, MD has had a more likely than not delay. For me three. In general all Tesla owners are a friendly group and if traveling through give you priority or at least this has been my experience,
This past weekend 1100 mile round trip all but one Super chargers had other vehicles two I pulled into the last spot. If not crowded always pull into a no adjacent charger, if 1A is occupied pull into 2, 3 or 4. You will charge faster.
Thoughts with long distance travel ... start in the morning with the car fully charged 100%. Drive to the furthest Supercharge or greatest time your bladder allows. Stop, use the rest rooms ect and charge to the next super charger (typically 15 or maybe 20 minutes), its now lunch relax and charge for duration of lunch. Repeat process in the afternoon and into the evening if desired. When you stop use a destination charger.
Whether a parking garage, hotel or residence while you are parked if still traveling charge to 100%. If not drop back to 90 or below until back on the road.
Use the trip tool. Find it amazingly accurate as it relates to charge.