Thanks all for the responses.
So far I've resisted the impulse to buy the Mavic Ksyrium Elites I found being sold online for $450. They're pretty, and light, and it's what the "cool kids" have... but I'm really not any of those things.
I need to remind myself that while a relatively strong rider, I'm not in my 20's (or even 40's) anymore and I'm not in this for competition (besides the occasional attempt to beat down a friend on a particular Strava segment). Buying something a little heavier, but that will carry a load and won't require frequent trips to the LBS for truing is probably the smart play.
Anyone else want to weigh in on going to tubeless? I'm in the San Francisco Bay Area, and goat heads are a concern on many of the local trails. I've been running Gatorskins (25cm) with tire liners, so I'm not going ultralight there. I'm just wondering if larger riders on road bikes find the move to tubeless to be better at combating flats, or as a way to recover that weight from heavier wheels?