Dynamite Ash Timeline Interpretation
I'm still going through it, but hang on. This is how I'm explaining why Ash remembers multiple continuations of Army of Darkness at the same time.
Army of Darkness: Forever led into the theatrical cut ending after Ash went through the vortex. After this, Ashes 2 Ashes occurs... then, somehow, 23 years pass before we get to Shop Till You Drop Dead. Blah blah blah, 818793 stories play out until The Long Road Home storyline. Ash rewrites the timeline so everything after Army of Darkness didn't happen, and in 2008 he forgets his Chosen One destiny.
This allows the reboot, Ash and the Army of Darkness, to occur. Because it disrupts the continuity of Dynamite's original story, I like to think that when Ash arrives in the past seven months after Army of Darkness, this actually creates an alternate timeline going from there to Ash in Space!.
Somehow, Ash eventually returns to his original timeline off-screen in 1982, where he gets arrested and Evil Dead: Regeneration plays out. This game actually doesn't suggest that Army of Darkness never happened. The first level is just an inaccurate flashback to Evil Dead 2. Can't find a single source that it ignores Army of Darkness or Evil Dead 2's ending. The logical conclusion to me is that Ash got arrested after the S-Mart Deadite attack.
The Army of Darkness vs Re-Animator: Necronomicon Rising crossover actually explains Herbert West discrepancies. The original crossover was in a timeline where the Re-Animator films never happened, hence why the lore doesn't match. After The Long Road Home, post-1982 events, perhaps even post-1300 events, were completely altered. This crossover shows Ash meeting the West from the live-action films and explains why Herbert recognises Ash despite the timeline change when they meet again in Prophecy.
Evil Dead: Hail to the King and Evil Dead: A Fistful of Boomstick happen afterwards, nothing much of note. A few stories in an anthology comic and a Darkman crossover happen before catching up with the main Dynamite storyline in 2008. Ash in 2008 doesn't remember events from 1982-2008 from either the previous timeline or the newly rewritten one due to making himself forget his Chosen One destiny... but then he remembers at the end of the story and I suppose his memories get amalgamated together.
The rest of the comics are mostly straightforward, though the second Xena crossover jumps forward 50 years in the future to a 109 year old Ash that isn't just alive but barely struggling. Uh... magic? Anyway, he goes back to 2016 and gains back his youth, so technically Ash vs Evil Dead Season 3 features an Ash Williams that is 50 years older than he was in Season 2. Was this intended? NO!

I threw in Ash becoming president in this timeline, too. A bit nonsensical since he's supposed to be waiting for Xena but hey, it needed to go somewhere and he's obviously not the president in the main reality.
Ash vs the Army of Darkness is clearly trying to be another reboot where the trilogy happened in 2017 but honestly, if you just assume Ash killed another Deadite in S-Mart in present day after apparently returning from 2093 post-Season 3, it doesn't cause too many problems. Death to the Army of Darkness! also fits present day fine if Ash actually did work at that S-Mart for 2-3 years, and that leads into him going to the Die!Namite Universe, which leads into the 1979 comic which validates everything being connected. I haven't properly got through Red Sonja vs the Army of Darkness, but I have a feeling the start of the comic could be part of the main timeline before Ash creates a new one trying to save Shelia. Archie x the Army of Darkness is inconsequential so that's fine...
The Evil Dead 2 comics concern Annie Knowby and a clone of Ash created from his severed hand. I would personally guess that the reason Ash's hand doesn't have a consistent history is due to Time Vortexes, Hell, or, uh... just plain magic. I'm not too concerned with that lining up. Other than the prequel issues with Raymond Knowby having modern technology, you can pretty much just assume that Annie and Ash (clone) left Hell in 2015 and there's no anachronisms.