You have to consider your timelines. Obi-Wan has been dead for about a decade in the time these Mando/Fett/Ahsoka shows are set.
Unless these shows are doing some time jump/reset or Obi-Wan encounters Ahsoka as a blue glowing Force ghost (entirely possible, and it’s the reason I assume we’ll see an appearance by Liam Neeson in the Kenobi show).
Jedi don’t die…they just turn translucent blue and pop up to offer advice/guidance when still-alive Jedi need it most. Going by that, it wouldn’t surprise to see Samuel L. Jackson in that form at some point in that Kenobi show. Obi-Wan was close with/knew both Qui-Gon and Mace Windu.
All I’m saying is…if they figured out a way to bring back Mark Hamill/Luke Skywalker(!), then anything/everything is possible. Especially within the realm of Force ghosts and ever-improving CGI/deep-fakery.
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