I think it was wonderful when headphones always worked, usually sounded fine (sometimes magnificent), and were available for $10.
> There was a whole cottage industry of DAC that you had to plug between your phone and your headset.
If there was, it was minuscule. I've never heard of people doing that in the wild.
> As a very deep hole, the jack was also a dust/lint catcher, almost impossible to clean.
Back then, the products were expected to be used long enough for this to become a problem. After a decade, I bet some of those holes were pretty dirty, although who would know. Modern portable tech does not have the disadvantage of durability.
> because of its length, it had a lot of leverage on the board, requiring fairly heavy-duty soldering to avoid damaging the board.
True. Can't deny this.