> The Plex Server has to transcode all types of formats to H.264 in real time. My old 2006 Core Duo 1.66Ghz Mac couldn't handle it.

That that's more than 10 years old. Your original point was that you're using a 10 year old system.

> They weren't transcoding 1080 video to H.264 real time in 2008.

Again you're comparing apples to oranges because most people wouldn't have had a need for transcoding 1080p videos from home servers back then. Most broadcasters still weren't sending HD streams or had only just started to. So a 10 year old PC in 2008 doing HD would be like a 10 year old PC in 2018 doing 4k.

>* My 2008 Core 2 Duo can run the latest software and the latest version of Windows well. Could those 10 year old computers run Windows 98 in 1998?*

The examples I gave were from around 1994/5 and as I had already cited they were running Windows 3.x (Windows 95 hadn't been released at that time). So yes, the latest OS.

> How is a watch that runs a phone OS that makes phone calls not considered more of a phone than a watch?

I'd already address that point as well. One word: "expectations". I don't expect a watch to be obsoleted after 2 years regardless of the tech it includes. If said tech means my expectations cannot be met then I simply will not buy any more watches made by that company. After all, I already have a phone; what I need is a watch.

> The difference is that my 10 year old computer can do the same thing as a modern computer - run the latest OS and software, has just as much memory and storage (HDD vs SsD) and has a slightly better display (1920x1200 vs 1930x1080). Can that 10 year old digital watch do the same as a modern smart watch?

I've already addressed that point too. Watches are not PCs (forget the technology and thing about it's form factor and what it's actual usage is). Thus comparing the two doesn't make much sense.

>* The only reason that my old Core 2 Duo is "future proofed" is because useful improvements have slowed down dramatically in the last 10 years. In 1998 the typical computer was coming with 32-64Gb of RAM and couldn't be upgraded to 4GB. My computer from 2008 came with 4GB RAM, the same amount as some low end computers today and can be upgraded to 8GB.*

Nope. I've already demonstrated that software likes to keep up with hardware. This it as true now as it was 10 years ago (even 20).
What's changed is:

o we've moved back towards a time sharing model where processing is offloaded to the cloud

o we've learned lessons about security after the mistakes of the 90s and 00s where PCs were basically just honeypots for malware. Granted we still make lots of mistakes even now (particularly around the area of IoT where we seemed doomed to repeat past mistakes) but in terms of actual PCs the groundwork was put in 10 years ago.

o software development processes have matured and also include better automated testing frameworks making it easier to detect problems and test on a wide range of platforms

o Microsoft also got their fingers burnt with the whole "Vista Compatible" thing on backstock Intels that clearly weren't capable. So invested more in the future releases of Windows to ensure that didn't happen again.

You could also argue that the pace of "useful improvements" in OS development has sped up over the last 10 years because more time has been invested in making platforms stable, secure and performant instead of just throwing new shiney feature after new shiney feature.

>* My 2008 computer has gigabit Ethernet. Which is still the fastest consumer internet connection.*

Another meaningless comparison because my 1998 computer had 100Mb ethernet, which was several orders of magnitude faster than the then fastest consumer internet connection. If anything I think the state of networking gear has stagnated because I was handling gigabit switches back in 1998 (with AppleTalk - yuk), which took forever to reach consumers and still many ISP routers only offer 1 complimentary gigabit port. Yet most offices / server rooms are still only on gigabit switches some 20 years later and most home users are probably on WiFi or Powerline adapters (neither of which will come even close to 1GbE). So I guess the real question is, how fast does one actually need their LAN to be? Either way, it's wildly off topic.