Atrain, if I absolutely HAD to take a SWAG at it, I would guess January 2013.
They're going to want to sell you the new Jelly Bean phones that are coming out this fall/winter. Maybe - just MAYBE - after that, they'll finally push out a JB OTA.
Rooting was/is a scary thing for me too. Even rooting veterans will tell you that if your pulse isn't racing a little bit in the process, then you probably have no clue what you're really doing.
But Wug's Galaxy Nexus Root Toolkit was amazing for me: You tell it what to do, and it pushes the ADB and fastboot commands to the phone for you. Such a time saver! Tell it to unlock, it does (wiping the whole phone in the process, so back up!). Tell it to root, it does. Tell it to flash recovery, it does.
Then you're free to flash away!
But I would say that my #1 reason for rooting isn't even ROMming... it's the ability to make nandroid backups. A nandroid backup takes a snapshot image of the phone's entire current state at that moment... system, data, boot, everything but the internal user storage. And if a malicious app takes over and screws things up, or a mistake is made flashing a ROM (it happens to the best of us), you can wipe the phone and restore the nandroid. It'll take the phone back to the exact state it was in at that moment, and it will be like nothing ever happened.
I had a lot of questions as a newbie. I read. A lot. And then I took the plunge. Having experienced what Android Open Source is, and the power that you can have over every aspect of your phone (not what Verizon says you can do), I would never go back to stock and stay there.
When you're ready to root, let us know. We'll guide you through the process and advise you. In the end, though, it's YOUR phone. We're not there. You are. And YOU get to do the leg work and the home work.
My 0.02 and aren't you glad you asked!