Bootstrapping using letsecrypt requires an internet connection and a public facing service. I can say that 14 year old me, who had books, a pc and no internet would have been screwed by this.
[1]: https://caddyserver.com/blog/caddy-0_9-released#easy-self-si...
I expressed dissatisfaction with the fact that learning to code for the web has a barrier to entry now that can be very difficult for various reasons. Learning To debug TLS issues is another problem in of itself which often takes a lot of years to fully understand.
A new programmer should be very aware of the tools that are available to make this easier. But 14 year old me with a php book and no internet did not have such luxuries and that was all I said.
The problem here is you are thinking about just yourself. Yes, it's hard to do learn all these things. It was especially hard back then because the the sources to learn were pretty crappy and taught a lot of bad things. That's part of the reason we have the 'exploit a day' internet we suffer from now.
If new web developers have to learn both protocol security and code development, it will probably mean less developers. Which is great for the ones that take the time to learn, they'll get paid more. It also is probably better for the customer, hopefully it will mean they are less likely to get served virus_porn_encrypt-your-computer.exe from your half baked website.
Tomcat and apache are still massively deployed. If you moved to nginx years ago, remember than it's still a new toy for a huge number of people. So caddy...
The only unfortunate thing is, that RHEL7/CentOS7 have OpenSSL 1.0.1 and mod_http2 requires OpenSSL 1.0.2. Thus no http2 there.
If you can create one, presumably for your internal network, with no public facing parts, how exactly does letsencrypt "screw you"? You can create and distribute self-signed certificates today, just like you could the past 20 years.
Browsers will still support HTTP in a decade (current low-powered network hardware and the like will still be around and need to work).