First of all a nitpick:
" It is the only “integrated upload tool” for Wikimedia commons (aside from the WMF-developed Upload Wizard)"
Technically you also have the original special:upload, and also that mobile thing thats less popular.
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One thing i would like to see in future gwt development is bringing it further in line with mediawiki coding conventions. There are several parts that do things differently than the normal mediawiki way, and also some parts that duplicate mediawiki code, but is subtly different (e.g. some of the sanitation code stands out in that regard). Ancedotally i believe this inconsistency with MW core code conventions is significantly reducing the amount of patches that interested unaffiliated developers would otherwise contribute. I also think that more closely following mw core conventions would make it easier for a wmf staff (or volunteer) who isnt previously familar with the code to debug critical bugs in emergency situations (e.g. things like the hhvm job runner bug).
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On the subject of code review, i believe a major contributing factor to difficulties last time, was development outside of gerrit, and waiting until the end to do code review. I strongly urge that all development be done on wmf's version control (because people watch what happens on wmf version control, and even if nobody is providing code review, they may still point out things that could be significant problems later) . I know first hand that getting code review, especially for non-wmf projects can be extremely difficult. If at all possible, i strongly suggest code review be done as incremently as possible.
Good luck with the grant. I really hope it goes through, gwt is an important project.
--bawolff
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