What would be the point, even if they should manage to shut all of them, there'll always be P2P.
I think something like
MS-DOS Shell (standalone of course, without being bundled in a whole DOS distribution) would be OK. As in: MS wouldn't give a damn. Though its use would be hardly more than nostalgic. I actually uploaded it to a Spanish AW site. Here we have Norton Commander for download, which belongs to Symantec all right.
About old Windows versions and even DOS, IIRC Microsoft has actually stated explicitly that they are not OK with their distribution. Even if they don't prosecute it at all, which is true.