I might shortly be in a situation where I'll need to commute on a weekly basis to ORD from DCA (and sometimes BOS). In looking at how many upgrades I'll acquire (as a 1K) versus how many times I'll be in a plane, I won't be able to upgrade leg I don't think. In fact, I'll run out of 500's fairly quickly.

My question is, for those of you that commute every week to a place in the 600+ mile range, how do you handle your upgrades? Do you try to upgrade every time? Do you only upgrade on Thursday/Fridays so you can drink? What do you do?