Gameplan
I think as long as you pay the insurance, and the deductible, you should be able to file a claim on a broken phone into the future past your contract expiration and keep unlimited without issue. Thing is, you'll be on a old phone for a long time. You will get the phone lust. You will succumb to shiny new phone voices in your head and you'll have to decide between unlimited, and shiny new phone at full retail cost.
I am not fully sure:
1. Verizon won't yank your unlimited after contract expiration. They could, but I doubt they will piss off customers more than they have to.
2. I'm not sure if Asurion actually allows you to insure your phone past the contract expiration date. I assume they would, they just keep collecting the monthly fee. They enjoy collecting monthly fees, but I don't know if they consider phones that old to be too large a liability.
My contract does not expire until May 2013. I am not eligible for an phone upgrade on Verizon's website until January 2013.
Looking on ebay, I can buy a used "clean ESN" droid charge for ~$140.
It seems I am rolling the dice if my phone breaks down the road and Asurion replaces it with a newer equivalent. We do not know if Verizon will then force me on a tiered plan or not.
For a gameplan to keep my unlimited data...
1. Should I wait for a new droid to come out, pay in full $400-500, then cancel the Asurion insurance and keep my existing charge as a backup?
2. Cancel the $6 Asurion insurance and buy a used charge for $140 now.
It seems #1 is better since I would be able to have the latest phone. The con of #2 is being stuck with the charge for years.
Thanks