Ask Paul: December 24 (Premium)

Happy Friday and, if you’re celebrating, Merry Christmas (Eve)! Here’s a holiday-inspired round of reader questions.
Why?
crunchyfrog asks:

I'm frankly surprised you'd be taking questions this close to the Christmas holiday, but cheers to your dedication.

Thanks, I originally meant to do this a day early, on Thursday, but I forgot. Plus, my son is arriving a day later than originally expected (today), so I have the time.
Tech nostalgia
As I've aged, I've become quite nostalgic over old tech in many categories. Over the years I have owned quite a bit of tech that was really cool and great for the time but eventually got replaced as things progressed. I often kept my tech in great condition and almost always keep original boxes just in case I needed to ship it back or sell it as original boxes with the tech fetch more on eBay. As time has passed though, many of the items were sold, traded in or just lost to time.

Same. And in part because I can use what I do for a living as an excuse, old tech has a way of just piling up and piling up, so I’ve made a concerted effort over the years not to hold on to things, or “collect” them, and make sure they ended up in the hands of people who really needed them and/or would take care of them.

I do still have a few items, like that Byte Magazine collection and the original Samsung Windows phone developer unit, but they’ll need to be exorcised in the coming year.

Speaking of eBay, I have found some really neat treasures and have to stop my self from buying old stuff that'll probably collect dust or fill drawers, but it got me thinking about a question for this forum:

Going back over early tech you owned, what devices were your most memorable from previous PDA's, handheld game systems and early Smartphones that you used to own? Say from 1995-2005.

This is a bit earlier than that timeframe, but I bought an Atari Lynx and several game cartridges to play on the plane rides to/from our honeymoon, but I returned it all when we got back because I really couldn’t afford it. And Toys ‘R Us had an incredible return policy. (Which basically amounted to, they would take anything back, including items you didn’t buy there. I’m surprised they’re not still in business.) I’ve always been fascinated by portable gaming, and my son and I had various Sony PSPs over the years. I recall arguing that if they had just adapted a two-stick design like console controllers early on, those could have been great devices for shooters.

I owned almost every single Palm, Handspring, and Sony Palm OS-based PDA ever made, and I was always fascinated by that kind of thing. The Sony units were particularly high-end for the day, as I recall. I also owned a variety of Windows CE/Palm-sized PC/whatever Windows Mobile-type PDAs and then smartphones over the years. The Compaq iPAQ, for example with a variety of sleeves for storage and connectivity. (And that huge two-card sleeve.) Also the Dell ve...