IMO, the way to go would be with separate CR2s for items that are radically different.  For instance, if you have a piece of chest armor which is styled for realism and another geometry which makes it much more "fantasy" oriented, then you should prob separate the two.  However, if you had a geometry that added more buckles and maybe slightly altered the abdomen section, you could keep them together.

The added benefit for the user is they don't have to load several, huge, CR2s for two characters wearing the same product but using different versions.  So, let's say the customer really wanted to have one style on one character and a radically different style on another, they'd just load what they needed instead of having a lot of memory overhead.  Or, if you have three .obj that yield a combined total of 81 different combinations of gear, the user doesn't have to load 81 in order to just get three of one style. :)

Could any of it be converted over to Poses? ie: Buckles poses which loaded the buckles geometry, etc.

PS - I'm looking forward to your product.  It sounds excellent.  Any object shots you can post yet?