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The easiest was to blow up gortash with smokepowder when he gots crowned xD
First of all, nothing was bugged for me. Second, because it's named specifically, "Busker" is very easy and almost effortless to do latest in Act 3.
That said, I'd say ~48/49 are achievable in one normal playthrough (the first), doing the "good" things (the aforementioned Tieflings can only be saved on a good run). Some require a bit of reloading and doing "the other thing", but that's not very problematic.
The difficulty related ones are not recommended for the first time; especially Honour Mode requires knowledge of the mechanics and how the game is played. So that'd be the second playthrough. As this can also be a "good" run, there are some longer achievements that pair well, like the other mentioned "Hot Date".
And the third run would then be the special character. I (and also the devs ;) would not recommend playing as that one the first time because it changes the story and events in the game quite a lot, so the lore stuff gets changed. With this one then the rest/"evil" achievement are a good match (esp. "Cannot be caged").
So all in all, if you don't want to make things weird and experience the game as it should be/is intended, you'd need 3 playthroughs to get them all. You could however do the longer good ones the first time and pair the special character with the Honour Mode, but that's maybe a bit risky for the first time HM (risky but possible - but also depending on which ones you didn't get in the first run, I guess)?
PS: that's of course all "in my opinion", so "grain of salt" and stuff...
Only took me over an hour because I insisted on trying it the hard way, just to see if it is possible.
Should be doable in fairly under an hour when you are in a place with more NPCs than Emerald Grove and use an actual Bard (respecced MC, respecced companion or Hireling).
Just load an existing savegame, talk to Withers if you aren't a Bard and play any instrument near crowds while going back and forth between places.