I use the shock pump that came with my fork (Rock Shox Reba). It seems to work very well.

... and +1 on tubeless! I went tubeless on my CX bike last year, and I went straight to tubeless when I got my MTB back in April. Once you've got the hang of installing/sealing tires (and you've spilled at least 1 quart of Stan's sealant on your garage floor), it's super easy.