I bought a palm pilot sometime in 1999-2000. Not a good purchase 🥲
I think i convinced myself it would help me be better organized. It did not.
The PalmPilot was really one big solution in need of a problem, IMO.
I watched one of our local school districts buy thousands of the things, only to realize they had no real use for them. They wound up auctioning the whole lot of unopened devices for a big loss.
PalmOS itself was pretty nice. But ultimately, there just wasn't that much you could do with one that made life better/easier. I owned the Palm V for a while, which had the antenna and supported wireless communications. Even with that, you were really limited. It had a lot of "wow" factor to show off to people, but was just one more expense to keep it active with a data plan and wasn't that practical.
I thought PalmOS made more sense when they started pairing it with the Kyocera smartphones ... but they did a poor job with making all of that stable. So you were perpetually doing hard resets on the phones when things froze up. Not a great experience like that.