I've been buying electronic devices, including plenty of Apple products, for over 30 years. If a device fails, it usually does so during the standard warranty period. Of the scores (more likely hundreds) of electronic devices I've bought, I've only bought four or five extended warranties that the sales reps talked me into. The only time it might have paid off was for my 2008 MacBook Pro. I think I paid $250 for Apple Care. The battery stopped holding a charge during the first three years (which was my fault), so I got an $80 replacement battery for free. The motherboard went bad two weeks before Apple Care ran out, which I think was due to the faulty NVDIA graphics adapter, but I couldn't prove it. They charged the $310 flat repair fee, which they said would have been $700 without Apple Care, but I still don't understand why it wasn't covered for free.
Had I purchased extended warranties for every device for which I could have, I would have spent tens of thousands of extra dollars over the years. Aside from the MBP, I can't think of a single device that failed after the regular warranty period ended but before the extended warranty period would have ended. Electronic devices are very reliable, in my experience. They usually become obsolete before they fail. (Anyone want to buy a working IOMEGA Zip drive and Jazz drive?) The standard Apple warranty on my Mac mini ran out last month. If it fails within the next two years, I'll have to spend $670 on another refurb to replace it. Although it's more than what Apple Care would have cost me, it's far less than the combined cost of all the extended warranties I could have purchased but didn't -- because any one of those devices could have failed, right?
To me, insurance is worthwhile only if I couldn't absorb the financial hit of not having it (i.e., for healthcare, house, and car). It amuses me when a sales rep touts the rock-solid reliability of a product, and then tries to sell me an expensive extended warranty, just in case the product fails.