Thanks for this! I found the new AppleCare very confusing as well. To me, it depends on the timeframe. The traditional "3-year" plan is actually a 2-year plan that extends the automatic 1-year warranty. Coverage for 3 years, yes, but what you are purchasing is a 2-year plan on top of the item's standing coverage.
By this logic, the annual plan should kick in at year two. At the end of three years, you would have paid just $198 (99 x 2 for years two and three, with year one covered by standard warranty). So you would actually save money on the annual plan (198 vs 279 bulk plan).
The $30 savings you penciled out means you are paying $99 for a year one warranty that duplicates the basic warranty that comes with the laptop.
You do get more now, with the accidental coverage for 2 incidents. But that should be prorated in Year 1, because the warranty coverage is already included (vs years 2&3, where the $99 buys accident coverage AND extended warranty).
My question is: when do you pay the annual plan fee? For year one (right away), or at the start of year two, when the warranty ends? Your column suggests its the former. That seems outrageous, but does make the standard 3-year bulk plan the better buy. Can you clarify @henrytcasey ? Thanks.