Thing is, if the fill ALWAYS starts on the 'one', whether you cue it up or ask for it immediately, might as well always ask for it in the preceding bar... Unless you are talking about two or three beat fills, with the 'one' missing, that you have to hit on the 'two' or the 'three' to get them to work...

Oy veh! That has GOT to be a pain!
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An arranger is just a tool. What matters is what you build with it..!