The main obstacle I can think of is licensing. Some of the components you would need to make a Wine setup functional (e.g. DCOM, IE) come with licence restrictions that could make redistribution legally dubious. However, you could ship the distro with a bare Wine setup and include something like winetools to allow the user to build a working system from scratch.
Having said that, I use a bare Wine setup to run the Windows version of Quake II, which enables me to play add-ons for which the source code or a gamei386.so was never released. It works well enough, but nothing beats Quake II running natively on Linux, of course!
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