So I am happy to report that this failure is fixed and the upgrade even seems to have fixed other issues :-)
Reviewing recent results: https://www.winehq.org/~jwhite/latest.html
We do, in fact, see some encouraging progress. I blame Alex, Zeb and Francois <grin>.
The Linux box is down to 6 clear failures (and has a bunch of intermittents that likely hide real problems too).
Adding Windows 8 and Windows 10 did increase our counts, but our consistent failures are pretty small (about 13), and maybe there is some low hanging fruit in there.... (although it is mostly ddraw type stuff).
Cheers,
Jeremy