Here is my story with asurion and sprint.
Last year I had a mogul (that I paid $300 for on ebay) had it bout 8 months or so then in january I stumbled across a thread similar to this about the mogul - touch pro upgrades. I didnt have ins on my phone but I called sprint and complained about a white spot on my screen, dropped calls, etc on my mogul. 15 or so different calls to supervisors and all the rest, got me nowhere.
Then I had my wife call the local sprint tech store and ask them what they could do for her. The tech told her to call sprint, ask for the $4 ins plan to be added to my account. He said that sprint wont want to do it, just insist they add the service. So I called sprint, and they DID NOT want to add the ins. she even told me it would be a "waste of my money" but eventually the CS rep did add it. Next day I called Asurion and filed a claim. They had me fax in a form saying I wasn't committing ins fraud. I faxed all the forms in, called to check the status of my claim, and they said no problem, we have a refurbed mogul ready to ship out to you

So then I just hung up (mogul kept dropping calls remember) 2 weeks went by, of me calling every couple of days and I finally got a hold of a nice lady who said the only phone they had to offer me was the Touch Pro. I paid my then deductable of $50 and said thank you.
Bout 4 weeks ago I saw on here where asurion is now upgrading again from the Touch Pro to the Touch Pro 2. so I already had ins on my plan, I called asurion and they were out of TP, so she offered the usual (treo pro, curve and snap) I said none of those had as good a camera or screen resolution as my touch pro. She wouldnt budge on anything else. I said thank you and hung up. This past monday I read on here where alot of guys were calling in and saying they were offered the TP2 over the weekend and were just calling back to confirm their selection. This was getting them new TP2, so I called too and the lady said no problem! So $100 later and a day later (got mine on tuesday) im a proud owner of a new TP2.
costs:
$300 - mogul brand new
$50 - deductible upgrade from mogul to TP1
$40 - ins from January to October
$100 - deductible upgrade from TP1 to TP2
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$490 - Total
New phone every year =
PRICELESS