The 60% figure comes from the Chrome developers and I believe it's the total of all displayed interstitials.
I don't understand why you think self-signed certs provide any security. It isn't "easier" to do a MITM, it's the same as with no SSL at all. Unless you have communicated the cert to your users out of band (no first time visitors) AND they are installing the cert themselves, it provides no security.
1) They didn't understand what the warning meant.
2) They have seen the warnings before in non-dangerous situations (like the clock being set wrong or a self signed cert).
In my experience, you have to treat your users like they are idiots or malicious attackers who will do everything wrong and the software still has to be 100% secure and still work. As you've pointed out, Blockchain.info sadly does not have this level of security yet, as it requires use of a secure passphrase and knowledge of two-factor auth and installation of a plugin. I still don't understand why you think the plugin is useless.
You seem to be taking the stance that it is an impossible task to trust users not to click the button "Hack me" button no matter how scary we make it. If that's true, then aren't you the one calling the users dumb?
If this is really about only promoting clients with perfect security, then I'd say that you can't promote any of the desktop clients either as they are all vulnerabile to key logging and the beloved satoshi client has difficult to manage backups. Tangent: I wonder how many coins have been lost by deleting/losing wallets compared to being stolen because of weak security.
It sounds to me like if a user is going to be unsafe with their computer and accept bad SSL certs and generally ignore any warnings that things are going bad (as the studies you have linked prove), then these people more than likely have compromised computers anyway in which case their funds in their desktop wallet are also at risk and we have saved them from nothing by getting them to fear web wallets.
The only secure solution is a hardware wallet that can interface with any client, desktop or web. Then the private keys are never anywhere that can be compromised by a hacker.