I started migration today on a 300 KLOC project and all CSS files had been 
converted without any major issue using the Css2Gss tool. The only exotic 
issue I had was a NullPointerException for *.css files that do not have any 
content: https://code.google.com/p/google-web-toolkit/issues/detail?id=9131

After conversion I was a bit annoyed updating all the @Source annotations 
still pointing to *.css files. You can't blindly run a global string 
replace of .css -> .gss so this took some time.
Also I did not add any gss=true attributes to UiBinder files because we 
simply have a lot of them and I don't want to do that work. I assume that 
this attribute is not needed anymore anyways once the GssResourceGenerator 
is enabled by default for UiBinder <ui:style> elements.

Currently we run the app with CssResource.enableGss = true and 
CssResource.conversionMode 
= strict and do not have any issues. Overall it took less than an hour to 
achieve that state.


So I think I would prefer the second option (delete the property and make 
GSS the default everywhere) but it would be nice if GWT would prefer a 
matching *.gss file for any *.css file referenced in @Source annotations 
(may the css file exist or not on disk) and print a warning in which 
ClientBundles that occurred. That way people could execute the Css2Gss tool 
and can start using 2.8. Deleting css files and cleaning up @Source 
annotations can then be done afterwards in smaller steps.


-- J.

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