Flew DL out of PDX with some friends right after new year's and the early morning check-in line inside was insane, so we (2 couples) stood in the curbside line which was still fairly long, but maybe only about 10 folks deep. I had actually never utlized the service before, but I understood tipping was customary, but I wasn't sure the expected amount. It was very cold and windy that morning, so the sky caps were definitely earning hazard pay, and I was keeping an eye on the people in front of me trying to glimpse the average tip. Wasn't actually able to see much unfortunately.
So my friends (the other couple) get to the sky cap, check in and apparently realized they didn't have any cash on them to tip. The sky cap said, "Don't forget that I'll be the one looking after your bags..." in an almost menacing tone, but my friends were like, "ooops, sorry!" and walked off.
They got a guilt trip, which I thought was a bit uncouth, but their bags made it home all the same.
I hardly check a bag when traveling so I don't think I'll use sky caps often, but it's always good to carry a fiver and some ones on you for tips.