I'm taking a shot in the dark hoping someone here has figured this out, because they haven't figured it out at winehq, which I know is the more appropriate forum to ask. But,no one knows (that I know of), so here goes:
Do you know how to get the wacom pen pressure to work in Adobe Photoshop CS5 using wacom tablet? It works fine in MyPaint, Gimp, Pencil etc. So I know this is a wine issue with the wacom pressure settings.
I can provide any information you feel is helpful in solving this, just ask.
Best Answer
the answer isn't easy, you need to develop or pay someone to develop on your behalf a wine driver which can use pressure information from xinput devices and deliver them to windows programs in the way they expect.
This project might take a lot of time or a lot of money to get written. But I know that it has not yet been written and needs artists to step up to fix the problem.