Palm Desktop still works fine today on modern Windows, just have to grab USB drivers: https://palmdb.net/help/hotsync-setup https://palmdb.net/help/hotsync-setu

Palm Desktop still works fine today on modern Windows, just have to grab USB drivers: https://palmdb.net/help/hotsync-setup https://palmdb.net/help/hotsync-setup On Linux there's pilot-link (command line) or J-Pilot (GUI on top of that). I don't love the UI for J-Pilot, admittedly, which feels a little rougher than Palm Desktop. A Windows VM is also a common approach. For devices, there's a dividing line between 68k and ARM. A 68k will feel more "classic" and will often get you things like AAA batteries and LCD grayscale screens with a bit of an e-ink vibe. Some models like Handsprings are expandable with more "modern" (for 2001) capabilities like extra storage, a camera, or GPS. Some Palm/Sony devices have SD slots too. Most devices of this age involve feature tradeoffs, however. You'll often find color, or AAA, or 16MB of RAM, but not all 3. For a 68k daily driver, you probably want something running OS3.5 or OS4 to avoid the limitations of the super early versions. ARM models (Tungstens, various Cliés, Treos, etc.) close the gap with smartphones much more--and some literally were. Color, higher resolutions, lithium, media support, SD, bluetooth, wifi, etc. These run OS5+ and having ARM under the hood unlocks an additional class of apps the older ones can't run. A reminder also to definitely tune one's expectations to the era. Truly modern connectivity requires fiddling and having no-to-rudimentary HTTPS support can make these feel more disconnected today than they originally were. Still, you might also be surprised at how many daily tasks today were achievable 20 years ago in a way that's generally familiar to us now.