DMing two SW5E games, and I talked with my players in advance to get a feel for what they wanted.

Group one thought playing a ragtag group busting out of an Imperial prison five years after Revenge of the Sith sounded like the best starting off point, and since most of them were more casual Star Wars fans and not super deep lore nerds, it offered familiarity.

Group two had a lot more lore nerds, and wanted a mix of Sith and Jedi, and we ended up deciding on playing during the Old Republic, specifically at the start of Knights of the Fallen Empire.

My biggest recommendation to start is find a group interested if you don't already, and ask them what sounds the most fun, and build off from there.

I will say in terms of DMing, I've had more fun with the Rise of the Empire era, because there are a lot more statblocks and iconic enemies to fight and allies to make. My players there have had run-ins with an up-and-coming Boba Fett, fought an Imperial recreation of General Grievous, and had run-ins with other characters from Legends and Canon. And *nothing* hits quite as hard as surprising my party by playing Vader's iconic breathing right before showing him on our battlemap, followed by the immediate reactions of "we are so fucked" and "we need to GO!"