Regarding resale value, I’ve always been of the view that the base models retain a larger percentage of their initial cost. 3 years from now, no one will care whether it is a 10th gen i5 or i7. Since we’ll be on the 12th gen, or perhaps even on ARM, all that will matter is that it is an “old” chip. There are some exceptions. I think the i5 is a worthy $100 upgrade to the base MacBook Air. But by and large, get the configuration that works for you today. If you know your needs are going to change soon (e.g. you know you will be taking on projects that require more RAM or CPU speed), then buy for those needs.
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Yes, when I ordered the i7 Air, it was primarily because that particular configuration shipped a little faster, and the extra $141 (with my corporate discount) didn’t matter to me that much. That said, I’m happy that the Ice Lake MacBook Pro came out during the return period for the MBA, since I like it better (except I’ll miss the gold color of the MBA, since it stands out but isn’t gaudy). With my same corporate discount, the Ice Lake i5 MBP was only another $141 more than the i7 Air with 16/512GB, and has: a faster CPU, 4 ports (and on both sides), a wider gamut screen, better speakers, and doesn’t weigh much more.