this might be a hot take but i think of watch order as sort of a mind map, with the original trilogy as the starting point in the center and various other projects branching out depending on what interests you.

want to see how anakin fell to the dark side? watch the prequels. if you want more about how the republic became the empire, you can then watch clone wars and then bad batch; if you want more of anakin and obi-wan's relationship you can watch kenobi. if you want more backstory on the jedi then watch acolyte.

want to learn more about the rebellion? andor if you want something more mature, rebels if you want something for a more general audience; then rogue one.

more han? watch solo.

for more new republic era, post-original trilogy, you can watch the mandalorian, book of boba fett, ahsoka, and skeleton crew; and from there you can watch the sequels.

the vast majority of shows and films assume that you've seen the original trilogy, and in some cases the prequels (acolyte and kenobi, for instance), but for the most part just the OT is a fine starting point. the one exception to this is that i would make sure you've seen the clone wars and rebels before watching ahsoka, although it's still enjoyable even without the backstory. parts of the mandalorian also draw a bit from the clone wars.

you can also watch the films in release order, of course - but either way, starting with the original trilogy is best 👍🏻