I have an old flatbed scanner that I occasionally use. I bought it in 2003 or 2004. For scanning I use an old 2010 Macbook Pro still running on MacOS X 10.6.8. The scanner software ist written for Power PC, and MacOS X is the last OS that can execute the software. The scanner still works perfectly fine. Some time ago I found out that there is third party software availiable that probably runs on recent macOS installations, but since I refuse to pay for it, I transfer the scanned documents with a thumb drive onto my M1 Macbook Pro. I tried to connect my recent Macbook Pro with my 2010 Macbook Pro via Bluetooth, but I couldn't get them to transfer files between them, although they detect each other in the Bluetooth settings. I suspect that it is a compatibility issue, as there is a huge age gap between both operating systems (∼ 15 years)
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Define "outdated".
My main workstation desktop that I use for most of my heavy lifting was bought in 2016. In the years since, however, it's been maxed out on the RAM that the motherboard can support, the ssds, the video cards, etc... So while it's now hit that bottleneck of "can't upgrade anymore because it's at the limit of what the motherboard itself can handle", I don't consider it outdated because it can still comfortably do what I want it to do.
A close second would by my Lumix G7 mirrorless camera. Old, yes. But still works perfectly fine. Records in 4K and still produces a better result than smartphone cameras because it uses actual proper lenses rather than digital software trickery. With mirrorless and DSLRs, the lenses are far more important than the frame (to a certain extent), so I don't see a need to upgrade that anytime soon.
My LG V20. No current phone can replace the functionality of it. I'm dreading the day the apps I use for work stop working on it and I have to buy some POS modern phone and I can't do half the shit I currently do.
My 2070gtx
Mines still chugging along in my nephews PC.
Baskets and wheels.