I have never bought insurance before. But when I just got my Hero, and when I get my Evo next month, I opted for it. Over 5 years, I have now lost 3 phones and had a 4th break. Not the hugest deal with the crappy phones I usually had, but now that I am playing in the big leagues, it is just worth it to me to spend under a hundred bucks a year to know I can easily replace it.
Plus, since I have been paying nearly $120 a month to Helio/Virgin this past year, my bill with Sprint even with the extra $7 and soon $10 for 4G is still less than I have been paying