Web developers - want a clean, extensible, sane system to code against
Major consultancies (e.g. IBM) - want lock-in, wide and cheap talent pool, and minimal changes (unless it's an issue they have)
Browsers - want to render whatever they see fastest and securely
Content developers and end customers - never want to have to update their site that they bought in 1995
So I guess the question is not if its ok for chrome to break the web for half the world its if its ok for chrome to impose this cost on site owners on behalf of users for the benefit of users.
Incidentally while there may be a lot of tiny sites that don't use https aprox 3/4 of page loads are already over https. Making myrandomhomepageaboutcats.com switch to https seems a reasonable cost for making the rest of the web more secure.