If there were "huge" benefits (for me), I'd jailbreak... but so far, I haven't read of anything that would compel me to (and I keep up on ALL the jailbreak apps - discussed here, anyway). I have everything I want (need) non-jailbroken right now.
Like llofte said, there's just too many negative outcries for me to consider it (right now)... and it's not a question of fear, or lack of confidence (I'm a web developer of 10 years, I think I can handle it). It's rather a matter of me not completely trusting the DevTeam as much as I trust Apple, I guess. People can repeat the fact that most problems are caused by user mistakes over and over, but I'm just not totally convinced (yet).
Contrary to what some very adamant people here have accused me of in the blog comments, I am NOT opposed to jailbreaking (just their stubborn denials that problems exist - whatever or whomever the cause). Maybe if future Jailbreaking features become far more numerous, while Apple continues not keeping up with wanted features, my feelings will change.