https://bugs.winehq.org/show_bug.cgi?id=50285
--- Comment #4 from Erich E. Hoover erich.e.hoover@gmail.com --- (In reply to Martin Storsjö from comment #2)
These two issues remain with the latest version of the wine-staging patchset. ...
Yup, thanks Martin - I had a chance to figure out the hard one (Case 1) over the weekend, but ran out of time before tackling Case 2. I should be able to get to it (and Case 3) this weekend and push out a minor update to address this bug and Bug #50586.