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im gunna pick the attain/connect cuz its teh cheaper ones of what you mentioned. each connect/attain is currently valued at 250 dollars (plus tax and all that other crap) so should you have lost 2 of these then it normally would have cost you 500 dollars plus taxes.
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FULL DISCLOSURE: I am in the insurance industry.
That being said, the price you are quoting is probably with a 2 year contract. Without, it is much higher. My daughter has a Samsung Stratosphere. On contract, it was free. Without, it was $499. (Worth "free" price....). She is in high school. Chance of loss, theft or damage is quite high. $6.99 per month insurance, $100 deductible. If lost /damaged year 1, $84 + $100. Worth the insurance. Lost/damaged year 2: $168 + $100. Still worth the insurance.
After year 2, when she is eligible for upgrade, insurance is no longer worth it.
In this OP's case, assume he got phone for free on contract. (Worth $250 off contract seems cheap, but we'll go with that....) OP loses phone in month 4. He/she paid $7 x 4 months ($28.00) for insurance. Puts in a claim, Asurion charges them $100 deductible for new phone. Now phone just cost him $128. REMEMBER THAT WITHOUT INSURANCE THIS WILL COST $250 (assuming this price without contract is correct ....) Loses phone #2 in month 11. Now that paid $7 x 11 months ($77.00) for insurance. Asurion charges him $100 deductible. Now has paid $177 + $128 ($305) for this phone.
Assuming he bought phone without contract, he would have paid $250. No insurance. Lost month 4. Pays another $250. Lost month 11....another $250...$750 so far...Are where I am going here?
As Chris Rock says, "insurance is 'in case sh*t happens'"
For those who never put in a claim, on a cell phone, 2 years is enough. (Few of us keep phones longer than that anyways....I am one who does....)
So.....on this OP's case, although they are annoyed with Asurion, they came out ahead of the game.....