After going back and forth every day for the last couple of weeks, I finally made the most cheapass purchase I could make (and barely got the wife to give the okay).

Nashbar had a 25% off sale and they're cleaning out their inventory of the Easton EA90 SL since they've released a newer version, so picked up pair of those for $325 bucks and some Schwalbe Pro Ones for $76 from ProBikeKit.

So going to give the tubeless a try. Will use my current race wheels for training and these for race wheels. Will be nice not having to adjust brakes since they're both 22/23 mm wide. Really hoping this sorts me out for a while.