The funniest thing about a crewed mission to Pluto, in my opinion, is that it would take something like a decade to get there. Having a living human past Pluto's orbit would be a huge achievement. Getting them back alive? More than doubly so.
xkcd
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Such an intersting planet as well
https://www.reddit.com/r/pics/comments/y0xceg/the_clearest_image_of_pluto_captured_by_the_new/

I don't care, Pluto deserves to be a Planet. Classification be dammed.
Maybe if we find some water on it, we can get the Orange one to visit and name the water.
need a voyager 2 orbiter orbiter so the orbiter doesn't get lonely when voyager 2 ignores it
Also a crewed Pluto flyby orbiter.
Perhaps Voyager 3 as 2 happened already.
https://www.youtube.com/watch?v=qYNIsgDrIRE
Although you might need to slingshot of Jupiter and Saturn at the right time.
It amazes me how our greatest minds were able to work this out with the technology and understanding they had.