Yes you can fill cupcakes 2 days before serving but that's probbly the most time that should elapse before they go stale. It also depends on how well they are iced. If any of the cake is not covered w/icing it will dry out.
would i eat a two or even three day old cupcake -- heck yeah -- i mean nothing wrong with a week old cuppie right? a little dry maybe...
however i would bake them off at the last possible moment -- or bake in advance and freeze them -- because i would know how the all the different elements would act after the thaw because i test all that stuff out in advance --
best to you
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