Steven,
I rooted my Eris back in May and have been very happy with it. My main motivation was to be able to have wi-fi tethering in my back pocket in case I ever needed it (I haven't yet). Overclocking is nice, but the phone was already fast enough for me. Apps2sd wasn't needed since Ivan's ROM had plenty of space.
Fast-foward to July 15: bam! got the Droid X and love it (still love and have my Eris). Haven't rooted it (yet).
Here's my reasoning:
1. The Droid X is already very fast and will be faster with Froyo: no need to
overclock (not really sure anyone will need to (gamers, maybe?))
2. Gigabytes of memory for applications, not MBs like the older phones: no need for
apps2sd (Froyo will have it already baked-in)
3.
Bloatware that exists on the phone isn't really hurting anything (at the moment); if I don't want it, I don't launch it; plus, the phone is fast enough and has enough memory they're harmless: no need to remove bloatware (other than to make me fell better)
4. There are some
root-only apps that I'd like to have, but the ones that I use occasionally, like drocap2, have alternatives (SDK screen capture); I'm sure there are other root-only apps that are really cool, but I haven't really had a great need for them yet
5.
Wi-fi tethering, would be nice to have, but I still could re-activate my Eris and use it; or I could just root when I need it (hopefully, this is still an option after Froyo is released). Or, one could actually activate/pay for it from VZW...
Just my two-cents...thanks for being a cool, phone-guide-dude!