Thanks Stefan, interesting thoughts. Don't forget to add/insert examples sometimes as otherwise it's very hard to follow through just "paper"... :( For example: the problems you point out are better understood through a concrete example.. And don't forget that the UIBinder has just came out, and far from perfect... but it does fulfills a need for a group of people (just like you use it for toy app's)... Maybe in the next release of GWT we won't use CSS files anymore for widgets, but rather some CssResourse (xml) file/annotations. I think a CssResource-Generator would be a great idea. BTW: you might want to post your idea's in the GWT contributor list. They are always open for good idea's.
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