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Also attended those two sessions—excellent each!—as well as some very useful discussions with Adam spread over a couple days.
My understanding is that your hunch is 100% correct. When you apply your new theme, with those newly defined custom styles, to additonal layouts, FileMaker has no way of knowing which objects should be assigned those new styles (even though objects on the layout may have local formatting that matches the new custom styles). You will have to go through and explicity assign the new custom styles to individual layout objects. Potentially painful (depending on how many layouts and objects), but surely easier than the alternative you've contemplated of rebuilding layouts from scratch! Keep that Styles tab open, shift-click to select objects with identical local formatting, and assign away.
I remember that Adam (maybe Andrew too) stressed the importance of thoughtful style naming, which will help the next time you reskin the solution. Then, Bob Shockey—did you catch his session?—demoed reskinning. It was highly dependent on consistent style naming between themes.
Thank you for confirming my conclusion. So far I've only been able to select single objects to assign the named style, not the multiples "with identical local formatting" as you suggest.
I did attend Bob Shockey's session. His is the next on my list to review.
Hopefully in V14 they will be able to automate the reassignment as the necessary info is all there in the XML of the CSS as Adam clearly showed.
That would surely be a great feature.
I can confirm Mark's observations based on my own experience. About the only time saver I've discovered so far is the ability to assign a style to a number of objects at once, as long as you intend them to have the same style. Other than that it's object by object, I'm afraid.