I've no idea as to what is preventing the keyboard from working, but I expect that problem is fixable.

There are a few possible paths for Wine ARM from here:

• In addition to the "make Photoshop run on my Linux box" Wine product upon which everyone tends to focus, the Wine folks also produce winelib. Winelib takes all Wine's Windows-apps-on-Linux tricks and rolls them into something Windows application developers can use to compile their applications for Linux. Linux-running end users then don't need Wine to run the app as it is all baked in. This is the current focus of Wine ARM development.
• As has been suggested in this thread, Wine ARM could be developed to support the running of WindowsCE applications. I believe the Wine ARM devs have discussed this possibility, but no one is pursuing it.
• Wine ARM could be tied together with an x86 emulator to run Windows x86 applications on Linux ARM, just as people in this thread want. I believe Wine PowerPC developers are/were working on something along these lines. I don't think anyone is for Wine ARM, and it does not sound like quick, easy work.