Mac users having to deal with HP printers. Tale as old as time. Sad Apple doesn't make printers anymore. I remember we had them in school, when I was in high school (mid-90s). They just worked. They all had cute names, you just go to print and choose one. It's still pretty easy in Windows... until it's not. Like how I know with Windows it's possible for me, on a Windows laptop, to browse the drives connected to a Windows desktop... but it's super confusing to set up. With a Mac, you just see the other Mac in Finder. Now, I think I had to enable it one time on each Mac sharing, and the first time, I had to put in the admin name and password of the sharing one on the receiving one... but now it just works. It's slower than I like transmitting data over WiFi (they're both M2 generation, so WiFi 6?) but it works pretty seamlessly. The drive with the newer content is a portable SSD, so better to eject it (ugh) and carry it over to the MacBook and copy directly from it, but I'm also lazy and willing to wait for WiFi.

I'm assuming that Discman is an MP3 model? I had one by Phillips. It was cool because it had a bigger buffer (antiskip) than regular CD players. You could shake the damn thing and it was hard to get it to skip. But playing MP3 CDs? It would never skip because it would just buffer the tracks a few in advance. These days, I rip all discs to low complexity M4A (AAC), they're slightly bigger than MP3 320 at a little over half the bitrate (192k). I don't think old MP3 players would play those files. I remember Winamp (which was recently ported to the Mac, I mean the OG Winamp) wouldn't do it without a plugin.

And the Game Boy Advance SP was the best handheld, until the DS Lite, which was basically just a wider GBA SP that supported more games. I had flashcarts in both its ports. While the GBA games had to be loaded from the cart in the NDS slot, the cart in the NDS slot had something like a 16GB or 32GB microSD card in it, so it basically had all the games I needed. And the homebrew stuff was cool, too. But the GBA SP was a little more portable.

(Now I have a 512GB iPhone that solves both problems. The gaming, and the music. And a few others.)