This is overblown, isn't it? That thing can't do anything that a public wifi couldn't, and yet everyone connects their laptops to those without hassle. SSL is nearly everywhere now...
If a user wants their free wifi enough they'll be happy to click through those pesky warnings that the root cert is not trusted. They'll probably not think anything of it if it loads as normal, even with a big angry red cross. The speed at which users rip though Windows UAC warnings is astonishing.
https:// with no extra options is still very much prone to downgrade/stripping attacks, and first-time connections to an https:// site are particularly vulnerable since a lot of the extra hardening options (HSTS in particular) can be nullified through TOFU.