If Squid can't proxy sites with bad certs in a reasonable way, that's Squid's problem, not a problem with HTTPS.
The fact that some open-source software can't do what you want it to do doesn't mean that there's anything wrong with other people trying to be secure. The most obvious solution would be to fix Squid, pay someone to fix it if you can't, or at the very least write a bug report to let other people know that you need it fixed.
The fact that some open-source software can't do what you want it to do doesn't mean that there's anything wrong with other people trying to be secure. The most obvious solution would be to fix Squid, pay someone to fix it if you can't, or at the very least write a bug report to let other people know that you need it fixed.