I do have one windows pc in my office. It runs quickbooks, so I get that.

I do recall seeing something recently that allows windows applications to be ran in their own windows, but in vm (not wine). My memory may be bad though.

I think the key would be cloning a central system that's fixed. I think the problems start to arise when different people have different setups. Thus, I'd make the build as robust as possible to avoid having a bunch of user specific issues. Companies do this with windows VMs and thin clients all the time.

But I get the issue you're pointing at. Trust me. I have about 20 computers running various builds, some general use, some for specific purposes. It is a bit of work to maintain, though I've automated a bit via cron.