If Obi-Wan hadn't said "for over a thousand generations" in ANH and had instead just said "for over a thousand years" (which would have fit with the PT, which implied that the Republic had only existed for a millennium), we probably wouldn't be having these discussions about technological stagnation. I agree that it's a little weird. Sure, having a massive 25,000-year long timeline makes it possible to do all kinds of different stories with different characters, but it's still kind of awkward.
I really need to catch up on Dawn of the Jedi
. I remember being really excited about that when it was first announced, but I haven't had the time or the spare cash to keep up with it.