Where Everybody Knows Your Name

This comes from a friend in New York City.

"I am a regular at my neighborhood restaurant. Whenever I go there, the waitstaff comps a round of drinks or dessert. What should I tip?"

Lucky you! Tip as much as you can. (Plenty.)

*

"Should I feel guilty about being able to cut the line at the same
restaurant listed above? I rarely go there on weekend nights because
it's so much more crowded than on weekday nights, but when I do, I'm
usually seated ahead of people who have been waiting at the bar. Is
this a breakdown of the implicit social contract I have with the
fellow patrons, or a validation of another separate implicit contract
I have with the staff there based on my exorbitant usual tipping (see
question above)?"

Make an earnest attempt to honor the other patrons' places in line but if the establishment insists, it's their call. Don't make a scene. Just go with it. Many businesses show their appreciation for especially valued customers, whether it's sitting a VIP in a special section or pre-boarding frequent fliers on an airline. Enjoy your status and be kind to the little people.