You won't get the best answer from me but I can help out a little. Jailbreaking is a term for the Iphone and Rooting is for the g1. They're the same thing.
I'd imagine the Iphone goes by jailbreaking because it allows them to user outside software verses Apple just wanting them to use theirs.
Rooting for the g1 refers to the root of the phone pretty much which is the linux commands.
After the rc33 update users no longer had root access to there phones which is pretty much a crying shame since having access to the root of it can provide so much.
I'm sure you've noticed that T mobile was last to put out the 1.5 update and that many rooted phones had it before. And this is one of the advantages of rooting.
You do not have to wait for your phone provider to push out the update because it works like this.
HTC makes the update but releases it to T mobile so they can add things like My Faves or whatever else t mobile does that no one cares about.
You no longer get the ota updates when you root, but it doesn't really matter because if you keep in touch with forms and all you'll most likely be first to have the updates before tmobile puts them out.
And again there are many other aspects to rooting I haven't covered but honestly there really is no disadvantage to rooting.

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