It all just kinda depends on what you want. I also originally rooted for the sake of wireless tether. I was stock rooted for about 2 days before I figured I would check for myself what the fuss was all about. I really thought that I liked the stock rom, but sense 3.0 is really nice i think. Some people don't like sense at all, some people like to switch back and forth. I've never really had any battery or radio problems (well MR1 was kinda bad for me) so for me its really about asthetics...I love my custom notification bar, semi-transparent app drawer, custom font and the general look of sense 3.0.
As far as updating, I don't think its really that big of a deal...I loved Das Bamf Sense 3.0 RC 4.9...I could have stayed happy with that for a long time, changed merely for the sake of change. The nice thing about the dev community is that they are always way ahead of what Verizon is going to give you. Even if OTA gingerbread came out today the TBolt still wouldn't have sense 3.0.
For everyone its a personal preference, even after you decide to try a custom rom, you will come here and ask which one to try and you will get a hundred different answers (my vote is for Bamf Forever btw)...then again you might just decide you like a phone that works and that you can use as a mobile hotspot and don't need that kind of customization and then stick with stock rooted.
Just do what works for you.