It's easy to Tramiel for not having vision but what you're describing simply wasn't a thing in that era. Computers were silos which where hardware incompatible with one another. And the few instances where a next gen machine was build with support for its predecessors, that generally harmed the successor more than helped as fewer developers wrote bespoke software for the newer platform (why would you when you could target all versions of the product line instead of just the lastest machine?). However that didn't stop Atari from having a go with the many revisions of the ST and, later, the Falcon.
Plus the ST and C64 were largely sold as games machines (yes, I'm aware of the popularity of using the ST as a MIDI sequencer etc) and consoles of that era didn't follow an upgrade path either (baring the Atari 7800 being largely hardware compatible with the 2600 but the 7800 wasn't exactly a success because of that).
Many accounts of history actually look more favourably on Jack Tramiel as they argue that had the American Commedore offices taken his lead (like the European division did) and sold the Amiga in toy stores as well as the usual places - as the Atari ST was sold in Toys R Us across Europe - then the Amiga might not have flopped in the US. And there is good reason to believe Tramiel's strategy worked as the ST was a massive hit and the Amiga had a lot more success in Europe and America after the European division of Commedore started copying Tramiel's business strategy.
Ultimately though, few hardware manufacturers from that era survived. Even Apple nearly went under (several times in fact, Microsoft had to bail them out on one occasion just to avoid a desktop monopoly). And IBM didn't exactly do well out of upgradeable machines as the market just got flooded with cheap clones which IBM got no cut from. So it's very easy to blame Tramiel with hindsight but in reality he was one of the few which had multiple successes.
But it was too little too late. I had a pretty expensive MSX capable computer in the late 80s, the Yamaha CX5 I used only for music because nearly all software around ran on different architectures like the C64 which was inferior compared to it. By the time it started to be widely known it would soon succumb to the ST or the Amiga.
Plus the ST and C64 were largely sold as games machines (yes, I'm aware of the popularity of using the ST as a MIDI sequencer etc) and consoles of that era didn't follow an upgrade path either (baring the Atari 7800 being largely hardware compatible with the 2600 but the 7800 wasn't exactly a success because of that).
Many accounts of history actually look more favourably on Jack Tramiel as they argue that had the American Commedore offices taken his lead (like the European division did) and sold the Amiga in toy stores as well as the usual places - as the Atari ST was sold in Toys R Us across Europe - then the Amiga might not have flopped in the US. And there is good reason to believe Tramiel's strategy worked as the ST was a massive hit and the Amiga had a lot more success in Europe and America after the European division of Commedore started copying Tramiel's business strategy.
Ultimately though, few hardware manufacturers from that era survived. Even Apple nearly went under (several times in fact, Microsoft had to bail them out on one occasion just to avoid a desktop monopoly). And IBM didn't exactly do well out of upgradeable machines as the market just got flooded with cheap clones which IBM got no cut from. So it's very easy to blame Tramiel with hindsight but in reality he was one of the few which had multiple successes.