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Instead of radio buttons for the different print options, why not make them checkboxes?
As in, I want to print multiple selections all at once. (and, in my case, I don't print them to paper, I print them to PDF -- so it's much easier / more helpful to do that if it's 1 document instead of 4 or 5 documents)
I might want to click the main character, the gear and ability descriptions, and the journal, print that to PDF, and then send that to my GM and/or game group (on-line game group).
Or, if I'm going to play it at a face-to-face game group, I might print all of it (spells and everything), so I have it all in one place. Maybe print to paper, or maybe print to PDF (to use on my iPad or Kindle).
If I'm printing to paper, I can see the current UI is just "do one after the other for all of the options you want". Then you just stack them up and staple it: no way to tell if it was 1 file or multiple files. But, when you want it in one exact file for digital storage, it's not really easily possible with the current print dialog.
Maybe there's a neat "join these pdf files" utility out there, maybe there's even one that's free, and maybe it even works on a Mac. I don't know ... and I shouldn't need to know :-}
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