As someone who has 90 segments this year, here is what I do (note that 40 segments on non-F planes, so it makes it easier):
First, I always look at the planes being used. There are tons of times when there are A319s and 757s used for flights an hour or so apart on the same route. I am too lazy to use the upgrade availability tools, so I just look at plane types.
Next, I use miles and other confirmed instruments to upgrade any long flights (e.g., IAD-SFO). Then, I save all my 500 milers for the short flights like you mention. For me, it is IAD-ORD, IAD-BOS, ORD-LGA, ORD-DFW that are my short ones.
If I start running low on 500 milers, I will buy a 4-pack. In my mind, I figure that I am only using one of them at a time to "top off" my upgrades.
Next, I often fly on Sunday afternoon to get to a Monday morning meeting. In those cases, I will add a few segments to the itinerary in order to accrue more BIS miles towards the 500 milers.
[It also helps that I have become pals with the corporate travel agent, and she seems to often find me some paper CR-1 instruments!!! 4 this year, in fact! Here's to making 1K in August!!!]
albatross
Originally Posted by magiciansampras
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?