What would the prime tails think about modern tails?
Interesting...
Well, anon, I'll be real with you. From what I've gathered thus far, Modern Tails' characterization is inconsistent at best, so I think it would depend upon which game Prime!Tails gets to know Modern Tails from.
For example, I think if we look at Sonic Adventure Tails, given the fact that Prime does incorporate games canon into its timeline (despite the confirmation that it DOES take place within the games timeline, with the inconsistencies that also poses with timeline stuff and characterization I think it's more helpful to analyze what games canon it clearly pulls from to form its own canon) Prime!Tails would see himself in this version of Modern Tails. Sonic Adventure Era version of Modern Tails strikes me as a plausible younger version of Prime!Tails if you only look at Prime itself and don't consider that Prime is meant to fit within games canon.
Likewise, if Prime Tails looked from SA era Tails, to Sonic Boom Tails, to Sonic Lost World Tails, to Sonic Forces Tails, and then to Sonic Frontiers Tails, I think the inconsistencies in characterization would also probably confuse him a bit (basically, "if these are all 'modern Tails' why are they so different in how they act or how independent they are?"). I think Prime!Tails can absolutely understand any given version of Modern!Tails' wish to be able to be as strong as Sonic and stand on his own. I get the vibe from Prime!Tails (especially compared to Nine) that he is a valued part of the team and can pull his own weight fighting, but that he isn't as effective as Sonic on his own (unlike Nine, who had to both learn to be effective in combat AND in strategic planning). So, to me, Prime!Tails is in sort of this in between phase. He can keep up with Sonic, he can fight on the front lines with others, he can sit back and play strategist or give advice, and he builds tools and fixes the Tornado, but (either perhaps from settling into his current role for so long or from coming this far only to stagnate) he isn't quite to the level of hero who can work alone and at Sonic's side effectively. In this way, I think he can understand how SA1/SA2 era and Sonic Frontiers Era Tails feel.
So...I guess my verdict is this. Prime!Tails would be simultaneously confused by the inconsistencies in characterization, but I think he'd actively try to sympathize with the versions of Modern Tails (either by relating to them with his past or his present as well as he can). With that being said, though, we unfortunately didn't get to see much of Prime!Tails in Sonic Prime Canon, so I think I could have a more solid answer if we perhaps knew more about him.
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