Kabooms & new cars reflect the migration from traditional audio device tethering due to the now ubiquitous personal audio devices all using the small 1/8" earbud jack. They aren't or weren't really intended for input/output cabling but being that's how people have been using them, manufacturers have adapted by incorporating that size as aux inputs. Even if 1/8" size jacks was present on older classics, they were frequently mono, not stereo jacks. In any event, input and output impedances when mixing older boomboxes with newer mp3 type players intended for earbuds don't always mesh well.
Anyhow you are looking at it wrong since classic boomboxes are almost 40 years old now and you are wondering why they didn't have the foresight to predict what direction personal audio would take 40+ years later?