The insurance coverage is a tough sell. It is actually extended coverage above the normal warranty which, on my 8800 ($529 Retail), is for 1 full year. Anyone who purchases this product on a Platinum MasterCard or Visa automatically gets 1 additional year of warranty coverage.
$6.60 per month x 12 months = $80 + $110 deductible = $190
Used 8800's are already on e-bay for $250 (no contract requirements) and new ones will be that price or less in 6 months tops.
You should expect to get a used or refurbished phone from the insurance company anyway.
The 8830 (same phone with added WiFi) is already slated making the 8800 obsolete in 3 months.
Blackberry has a BuyBack program which encourages people to upgrade every year, ensuring a strong supply of used yesteryear product availability (notice how many people on this site have had 5 or more BB's in as many years).
So unless you plan on Losing this phone in the first 6 months (and you know your personal history of losing phones, sunglasses, purses, etc), its hard to see how you could so much as break-even, knowing that your getting old technology for a hefty price-tag for insurance.
The insurance company had to set the price high enough to cover all business users from simply "losing" their phone at the end of their 1st year (typ business contract length, which is diff than personal 2yr plans), and one should accept that Insurance Companies are not in the customer service business, but there to make money.
Know your own responsibility level, and know that you will be able to replace the phone with a myriad of reasonably priced options soon with little sting to the pocketbook.