I agree that it would be way too cluttered to do a separate timeline entry per episode... esp. for more long-running series like the Clone Wars.
As for articles... one per season could be helpful from a discussion standpoint. While they probably will be all interconnected through the series, a lot of times one season will have its own "entity" per se. And since the Disney + shows particularly will be shorter - I think the Mandalorian is ten episodes? And Favreau has said he's already working on season 2. While I saw the Obi-Wan one will be a 4-episode/part miniseries - I can't imagine it getting too messy. Even for the six, soon to be seven, season of the Clone Wars, that would probably get a bit chaotic if all of them were mashed together.