Entirely agree, although I think it varies by make / model. Roughly look for whenever a particular car got OBDII, which makes diagnostics way easier (and was kinda the perfect level of digitization, again in my opinion), through (as you say) whenever they started digitizing the cockpit and/or (which oddly - maybe? - coincide, in my experience) manufacturers stopped considering ease of maintenance in engineering decisions. In general late-1990s through 2005-2010. Cars since that decade (or so) are more sophisticated, at the expense of far, far shorter useful lifespans.
Mid 2008s saw a lot of cost cutting after the financial crisis, and then some very weird engineering decisions to deal with increased efficiency laws that made for much more complicated engines and transmissions even in smaller cars, if the smaller cars even continued to exist.
Early 2000s JDM coupes will always hold a soft spot in my heart, even though they've mostly rotted away at this point. I used to say I was into cars but these days there's nothing that inspires me at all, I'd be happy just to have a reliable electric box with 4 wheels.
Interesting. I kinda skipped that era of cars. Went from a mid-nineties Miata - which I still have, mostly maintain myself, and will never sell - to a 2015 CX-5, which I like, and seems well-made, but isn't exactly friendly to DIY. It's barely had any problems, though, through 150k miles, so that's not exactly a complaint.
No question, though, my next utility-car will be electric, and (though you'll have to pry it from my cold dead fingers) I expect my Miata to be the last ICE car I'll ever own.
