It'll either be Smile Isle or KK Mania, I feel like. Smile Isle because it feels like it takes forever to get villager requests nowadays, KK Mania due to it taking 2 years to do.
The way things look now, probably smile isle. I do sometimes forget to sit down for K.K. in the evening though. There's also two achievements that are still entirely blank for me, I suspect that those two are going to be seasonal but if I'm wrong about that then those could also take me a very long time, I suppose.
The ones that have high numbers for simple activities like crafting/gathering I can probably do eventually. For example I'm currently working on crafting tools, since it's tree shaking season!
Ooh, that's a difficult one. Like most others here, probably K.K. Mania. The concerts are just too big of an interruption, too long, into the gameplay. I want to play and do stuff, if I wanted to sit around watching things, that's what television is for. So far I've done only 14.
It might also be Smile Isle because right now I only have villagers that I don't want to gift random deliveries to, so I'm completely dependent on lost item quests and those seem to be very random. One week I can have 3 lost items, then there's weeks where I won't find any. Which makes it very unpredictable to say which one of the two I'll finish first.
(Small note: I'm not a pure 'non-time-traveller'. I time-travel to different times on the same day from time to time. I also travelled back in time to get the miles for the first bug-off because I missed that. But I'm sure I'd have completed the nookipedia and bug-off goals before KK or Smile Isle even without time travel)
I think the catch 3000 bugs/fish will take the longest since I hardly do either nowadays. Also probably the craft furniture achievement. I barely ever do that. My villager roster isn't set so I think it's entirely possible I'll finish the birthday one long before the other ones I mentioned.
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Oh yes, smile isle too. Since I am so selective when choosing which errands to complete for my villagers... not to mention how rarely they ask for favours in the first place.