So 2 weeks later...
I pre-spent my Christmas bonus.
Waves NX: Seems pretty good at resolving the panning issues that come with using headphones (the isolated ears).
Beyerdynamic 990 Pro Headphones: I needed (wanted) new headphones, these had decent reviews and I found a realtively inexpensive pair. They sound and feel great. Plus, they're on Sonarworks' list of pre-calibrated models.
Sonarworks Headphone Calibration: This seemed to have a minimal benefit, but for the cost I'm glad to have it.
Between those 2 applications, my mixes are sounding more reliable when played on other sources. I think they're both worth having, and they cover completely different aspects of the mix well.
Thanks for your help guys!