There are some tech purchases which, even if we later upgrade to something different, we enjoy the time we had with them and feel we got fair use of them. Then there are others which in hindsight we regret

Where do your various tech gizmos of yore fall on the spectrum? For me...
1) Alphasmart. Don't regret it. I bought one, then won one in a contest and sold the one I had bought, so I basically got it for free. It was a great device for me and when the Neo came out, I lusted for years before finally scoring one on ebay for under $100 and selling the Alphasmart.
2) Alphasmart Dana. I do regret this one, even though it was pretty cheap. I regret it because I could have gotten by just fine with the Alphasmart I already had. I wanted the Dana because they were plugging it as a great ebook reader since it came with a widescreen-enabled version of eReader. It is the first device I bought for the specific intent of reading ebooks (I had previously used a Palm PDA for that purpose). And...the screen has such a massive glare that the widescreen abilities were a total waste. It was brutal to read on. I still use it from time to time as a writing machine and it's good for that, but I could have just kept the Alphasmart. What I would get for it used is so low that I just keep it and mostly use it at Nanowrimo time.
3) eBookwise. I do regret this one also. It was a very pokey device to get content onto and its bookstore is terrible and has one of the most restrictive DRM schemes I have ever seen. It was big and clunky. It had its day for me, and there was a time I did use it often. But when I finally did sell it, it was at a huge loss compared to what I paid for it and I should have just bought the Sony in the first place.
4) Netbooks. These I also regret. I bought an EEE pc when it first came out and it died a painful death within a year. First, the battery completely went. It could not hold a charge and literally would start complaining after 1 minute being unplugged. Then the power cord had such a poor design that the prongs stopped registering they were plugged in so that was that. I gave it away to a guy who already had one with a power cord he could use with this; I couldn't sell it since it was so defective. I replaced it with an Acer which has been fine, but I don't use it enough and it's basically been little more than a glorified jukebox when I do music with my students. The year after I got it, our school got laptops teachers can sign out, so I could have just put my MP3s on a memory stick and used those with a plug-in speaker. I don't think I could get much if I sold it, so this is just going to take up space for me.
5) Sony 505. I don't regret it per se as I got good use out of it and read many books with it. But especially in light of the new Apple product, I don't think I will get a very good price for selling this and I was hoping for that to subsidize the cost of my new Kindle. So in that respect I am disappointed and perhaps I should have soldiered on with the eBookwise until the Kindle went international.
How about you, what is your device history like and do you regret any of your purchases?