> A personal website made of .html and other files in the past would last, literally forever.Web serving has always had moving parts, and there has always been some maintenance required to keep sites up. I agree that HTTPS increases the burden here, but not from zero.
> at some point that complex stack of software (who's complexity is hidden from the user) will break
Sort of? People definitely screw up their HTTPS configuration from time to time, or run into bugs. But the acme software is very reliable, so this is rare, and if it does happen blowing your existing configuration away and starting fresh will fix it.
> And not only does it make them more fragile but it makes setting up a website for the first time much more complex.
If you want to set up a website with minimal steps you generally get someone else to host, at which point they are dealing with HTTPS. If you want to do it all yourself HTTPS does add a step, but it is small compared to all of the other steps involved in setting up a server.
> The increased centralization will inevitably lead to increased pressures, social, political, and otherwise on LE to censor, revoke permission, or otherwise cancel the accounts of law breaking websites.
The US legal system cannot currently compel Let's Encrypt to refuse service to lawbreaking sites, and even if the law changed here you could get a certificate from a CA in another country.