It really depends, if it's a place I go to or pick up from frequently I will, especially locally owned places. I've found there are less mistakes with your order and seem to take better care of me. When I lived in Austin, there was a great little Chinese place I would pick up from 1-2 times a week and they took great care of me. The owner and staff would always throw some extra stuff in for me to try, they had Americanized Chinese food but specialized in more authentic Chinese food as well. It wasn't unusual for me to order a dinner and a soup and walk out with 2 brown grocery bags of take out, especially when they were doing dim sum. One day I went to pick up an order and the owner takes me to the kitchen and opens the fridge and there are 2 big kingfish in there. They had gone deep sea fishing the day before, he cut me 4 big kingfish steaks and wrapped them and gave them to me to grill later. They were great people and the food was awesome.
For pizza deliver now there is a 2.50 delivery charge that doesn't cover the tip. So when them bastards want to start taking 2.50 off my check for carry out, then I'll tip.
I appreciate the advice guys, and I came to some conclusions.
1) At no point will I be fixing my ceiling.
2) If you are a regular at a nice place which is the deal here, I like the "rounding to the nearest round amount" route. Last night's meal was like $23 something including the 6 pack so I did that, and wouldn't you know it I ended up chatting with one of the cute waitresses about how she likes Sheetz food when she is drunk late at night.
3) Fast food, coffee places, etc. no tip. No Starbucks either unless I'm trying to get in someone's pants. Nice place a tip though.
No real need to tip for pickup, they make a regular hourly wage. If the hostess or counter person is good/polite then I'd toss a buck or two in there. If she's hot and you wanna score some points, toss a 5 in there each week.