I realize that this is a subjective question, but I'm curious as to which approach to replacing gear (Macs, iPads, or iPhones) makes the most sense to you financially or in other ways. My approach has always been to buy the best model I can afford, to keep it until it dies or becomes unusable for my needs, and to either sell it for a pittance or give it away to someone with lesser needs. If the device is upgradable, I upgrade it over time as much as possible. The most extreme example was the trusty PowerMac G4 Sawtooth I bought in 2000. Over the years, I upgraded the main hard drive twice, added a second hard drive, replaced the CD burner with a Superdrive, increased the RAM, upgraded the processor with an OWC card, upgraded the graphics adapter, and added a USB 2.0 card. I kept it until 2008, when it finally became too slow for my needs, and gave it to my dad, who used it for two more years until it died. Then I bought an early 2008 MBP. I soon maxed out the RAM and replaced the hard drive with a higher-capacity one. Over the past year, it's started feeling slow to me. I've thought about replacing the HDD with an SSD, and even replacing the optical drive with a large HHD, with the idea that I'll get another year or two out of it. But I can't increase the processor speed, and the logic board already went out once (two weeks before AppleCare expired). Upgrading my PowerMac was satisfying, in a geeky way, and it spread out the cost over almost 8 years. If I add up the cost of all the upgraded components, though, I'm not sure I came our better financially than if I'd sold and bought 2 or 3 new Macs during those 8 years. The days of upgradable computers are almost over, it seems, but the same question still remains: Does it make more sense financially to buy a device, keep it as long as you can (by which time, it has little residual value), and then buy a new one or upgrade every year or two, selling your previous model while it still has high resale value? Apple products have high resale value, but I don't know from experience whether it comes out to be a wash i.e., spend $2,000 every 5 years on a new Mac (because your old one had negligible resale value), or $400 per year to upgrade to a new one (because you sell your previous one for $1,600 each time). As for non-financial factors, upgrading frequently ensures that you have the lastest tech, which you may or may not need. On the other hand, selling stuff for the best price can be a hassle. I'm leaning toward taking the "upgrade more frequently" approach in the future, but I'm curious about other people's opinions and experiences.