I tend to evaluate my cars when I send them to the crusher. Cost up front(used), repairs and gas, total years/miles. I can't tolerate too many breakdowns though.
That's what's kept me happy with mac stuff for decades. The only time I questioned that was the first couple ipods we bought for gifts for the teenagers. I was ready to bail out as they didn't hold up as I expected apple products to do.
But those problems were quickly resolved(and they got much better, fast). Home macs we've had lasted forever, we only bought a few in 20 years, just added parts to keep them current. Always added memory as it got so cheap, that kept our macs working forever.
When there was a problem, they fixed stuff quickly, free with a guarantee, reasonable without.
We splurged 5 years ago on 3 macbooks. They're all still going strong(2 in college, one for my business including CAD work, and home use), zillions of hours. I had to put a new HD in mine this year, but the kids still find theirs are fast and up to date. I expect another year at least which will put the cost at about 150 a year, if we throw them in the trash(we won't someone will use them to death). Not bad for the hours they get used. That's what I want for my dollar.
Our kids could be chips off the old block (cheap), but they're very happy and not needing upgrading.
Our sons macbook was stolen over the holidays, he bought a Mac air(after working for me over his Xmas break) as it was a bit less than the macbook. I keep asking him what the downside is and he can't seem to find one. But he loves the size and how it works. I suspect he'll get a long use out of it, if not, I know a few that will gladly inherit it.
We still have older ipods(mom and dad inherit them) and they work fine and are a cinch to get the stuff on the macbooks and onto the ipods.
I'm sure you can get the same value out of other stuff, but I tend to stick with something that's worked well for so long.
No iphones yet though, they're just too expensive on a monthly basis to make sense for us.