Step 1 is to find out what tech support and policies are at his school. When my daughter attended Drew, she bought the laptop from bookstore(?). and she had full support as long as she attended.
I know nothing about Dell support, but Ideally you'd want something akin to Apple Genius Bar - that can take care of many problems on the spot. That, for me, would be a compelling reason to go Apple.
Laptop should come with a one-year warranty which can be doubled by using most credit cards. If you buy the laptop at Costco the basic warranty is usually two years plus whatever the credit card offers. If you want an extended warranty do not buy it a best buy but look for a deal on a square trade warranty.
We are not generally big fans of extended warranties, but we have gotten the Dell 3-year contracts on our laptops and in at least half of the cases have gotten benefit from it, so will probably do so on future purchases as well. (We have purchased our computers direct from Dell, though. Perhaps BestBuy has something with their GeekSquad that would be better??)
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The Boy is shopping for a laptop at Best Buy with Mr. Z... he's done his research and is getting a Dell laptop with a touch screen for college. (I thought he should get an Apple, but he's looking at half that cost.)
Should we invest in the extended warranty?