https://bugs.winehq.org/show_bug.cgi?id=44942
--- Comment #3 from Henri Verbeet hverbeet@gmail.com --- (In reply to Rosanne DiMesio from comment #1)
The checkbox was disabled because official WineHQ staging releases stopped. While work has unofficially been done on bringing staging up to date, there are still no staging packages on dl.winehq.org, nor have I seen any official acknowledgment of Alistair as the WineHQ staging maintainer. If and when that happens, I will send a patch to re-enable the checkbox.
There's https://www.winehq.org/pipermail/wine-devel/2018-March/124819.html, which nobody objected to, although I think it would be good for Alexandre to explicitly acknowledge that. That still leaves the packages, of course.