Intelligently Renumber Pins

You don't need the wizard for something that simple. Just add the pins manually. Just pick a padstack, qty, spacing, order and that's it.

Oh, in the "Options" pane on the right side?  That makes sense.  Thanks!

Next stupid question, is there a trick to create a drawing boundary, or should I just draw some lines on the Board Geometry layer and move them around as needed?  On a new symbol it just keeps telling me "Pick is outside the extent of the drawing" and won't let me place a pin (or array of pins).

The Layout>Pins will let you place pins, rather than use the Wizard, and Options will be "in play" for this command. You could also use the Export / Import, CSV Pin File to renumber existing pins. The issue with "placing anything" is probably down to the Design Parameters, Setup>Design Parameters, Design tab, set the Units / Size / Accuracy to get a "decent" page size to work in, much bigger than required is not an issue, also check that the "Left X" and "Lower Y" give you some area to work around the origin, negative values of, say, 3-4 inches (3000-4000 Mils, or about 100mm) are usually sufficient but this will depend upon the symbol size! The page size that the symbol is designed with won't impact it's use in PCB Editor. (Provided that the PCB Editor Drawing Parameters are sufficient) If you are design a "drawing blank", Drawing Format / "whatever" are the subclasses to be drawing on. You typically wouldn't have a "drawing blank", drawn border, around "other" symbols, like footprints, in the design.

Awesome, I think the Design Parameter window was the part I was missing. Suddenly things are starting to make a lot more sense. Thanks!