Surprised to see the Palm not getting the love. My mom got me a Handspring Visor around 1995 after seeing that all her medical students were using Palm OS devices for reference books etc. To this day I think input on iOS devices would be easier if they adopted Grafitti.
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A friend of mine once asked “who needs more than a 2 megapixel camera”? (I had a 3 megapixel one - my first digital camera - at the time.)
Long ago - and bear in mind I work for a big computer company - I coined the epithet “all new products have unlimited capability on the day of announcement”. (That comes of reading Marketing foils 
/ slides uncritically.)
The serious point - that we’re all making - is that use cases and limitations emerge with use.
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I have a Nikon D3500 that I bought for an African safari. It served us well there – but I have barely used it since.
My iPhone XS takes photos that are just as good, to my eye, with the single, very important exception of lenses. There is no practical way to attach a lens to an iPhone – and yes I have tried the Moment lenses.
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I don’t know about spectacularly wrong, but I really bought into wired Internet being the only way to connect and didn’t trust WiFi speeds or latency for several years of its initial viability. As recently as 2014 it was important to me that a laptop have a dedicated Ethernet jack. Today I do carry an adapter for Ethernet in my bag, but I haven’t used it in a few years.
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I still wire everything I can, if only because moving as many devices as possible to Ethernet frees up WiFi bandwidth for devices that don’t have that option.
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Oh for a wood grain finish iPhone 12 Pro Max 
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Like so many things in this thread I can mostly claim the opposite. I started with a Casio Digital Diary which I absolutely adored, though I didn’t have so much of a life back then that I actually needed it. I progressed to a Palm III then IBM WorkPad (Palm V). I still have the latter one and recently was able to extract some data from a backup I found on an old hard drive which helped me pinpoint an historic event in my life! On my iPhone I still struggle with too much choice on calendars, to do lists, heck, even where to store my contacts (Google versus iCloud). The Palm life was so much easier!
There must be something I was fundamentally wrong about but I cannot think of it at this time. My specialty is actually buying stuff that I end up using a handful of times before they become obsolete. Like my awesome CompactDrive PD70-X which I think I used about 5 times.
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Probably not mentioned because it wasn’t spectacularly wrong! 
It didn’t evolve, like many, after Apple came out with the iPhone and spectacular marketing! I loved my Palm(s)! I had the original with the 1MB memory (only a Luddite would have the 512k! 
) and then on the to the rest to the V. Still like the form factor.
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3rd! I thought I was so ahead of the curve with those minidiscs lol
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The Apple Newton. Never took off. I essentially never used it.
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It took me way too long to get on the iPhone train. I didn’t get one until the 4S. I didn’t think it would flop; I just didn’t think it could possibly be better than the Android phones I was used to. I was very wrong.
I’ve also been proven wrong about 4K, which I figured (based on my still-correct math about the practical need for it, given viewing distances and pixel sizes on TVs) would be mostly a flop. Honestly, I thought 4K TVs would be largely used for 3D imagery, so the viewer could get full 1080p resolution for each eye. I was spectacularly wrong about all that.
Many, many of what my wife calls my “magic beans” gadgets. But, I’ll go with Intellivision, when the masses were buying what I thought was the far less cool Atari.
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Make that 4 people
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I loved my Palm devices - latest was a Palm Tungsten with actual internet connection. While it never delivered the “real” internet, at least some of the apps could connect. I used it and a 2-way text pager and a cell phone to do product support for a few years. Looking back, it was a nightmare. The first week I had an original iPhone and a customer called to request a password reset while I was in line at security in the airport and I logged into our server over wifi and reset his account, I knew things had changed by several orders of magnitude. PalmOS took me a long way, but iPhoneOS1 started a new paradigm that I’ve never regretted.
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I have to confess…I am guilty of the same crimes. 
Especially the Palm, that one quickly found it’s way to the bottom drawer t never see the light of day again.
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I bought a Denon DAT (digital audio tape) deck just before burning CDs at home became affordable. You do NOT want to know what a high end DAT deck (Denon DTR-2000) cost circa 1992! (And I can’t tell you because I purged that painful memory long ago)
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WindowsRT… was at the launch event in Times Square and all to get my hands on that first night. My dream was always what we have now in iPad Pro.
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DSLRs. In 2017 I was telling people it was iPhone computational photography for me from now on, no more DSLR. Then the eclipse came along. Rushed out for a new DSLR, rented a lens, photographed the eclipse, learned to process the photo in Lightroom / Photoshop and was back in DSLR world again, and then this year got fully immersed in astrophotography.
iPhone is still very useful during astrophotography - there are many necessary apps, I shoot B-roll of the equipment used as well as night mode shots of the sky, I could control my sessions from the iPhone as well but iPad is better for this as it has a bigger screen.
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Me too friend, me too.
I wasn’t wrong on that one. Still shoot most photos with a DSLR and phones are not even close.
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