The average persion can pick up a ChromeBook and use it, despite the UI theme looking nothing like Windows.
So I don't think that is the barrier to Linux adoption. ChromeOS kind of is Linux anyway, maybe not GNU/Linux.
Most people, the problem is, they ask if it runs $x which is very important for their workflow, and the answer is very often no.
Wine usually doesn't help. I can think of very few things that work reliably on Wine and don't have a better native alternative.
I actually think that making Linux look like Windows would make it more confusing. Go into one of the many Windows control panels, which are not the finest examples of software design, and try to administer a Linux system in the same way as a Windows system. It won't work, because Linux isn't Windows.
Normal people don't do that anyway, they ask people like us for help.