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Root Rooting advice (G1)

Okay so here's my problem. I've had this stupid G1 for nearly six months and I have the two year contract with added insurance. I'm interested in rooting to 2.1, but I'm concerned about voiding both the warranty and the insurance policy (which is expensive). I'm not really concerned about bricking or about the overall procedure. I'm about to leave for college so I really don't need to have to pay for a new phone if something goes wrong with it. Should I go ahead and flash the rom or should I wait until the update comes out (if ever)? And how does the flashed rom compare to the current OS? And if I get the 2.1 rom, can I also use Apps2SD at the same time?
 
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