If your car is still charging when you walk up to it, the charge port is still awake, so clicking the button on the charger will unlock it as long as it senses your phone nearby. If your car is done charging, the port falls asleep, and needs to be awakened by the computer (by opening something) before the charger button will work. Supposedly, Tesla is working on fixing this, but AFAIK it's still an issue for people.
Ironically, this means people charging off a normal wall outlet are usually getting a better unplug experience, because the car is almost always still charging when you come back to it. I experienced this change in behavior when I upgraded from a normal wall outlet to a dedicated 40A circuit.
To answer OP's question, here are the guidelines I live by:
- Don't feel like you have to fill it up completely unless you're about to go on a road trip.
- Try not to let it run down below about 20-30% too much if you can avoid it.
- Plug it in whenever and wherever it's convenient for you.
- Otherwise - don't overthink it!