I'll have to clarify right at the top that I have not previously commented about Caddy, and I don't care about one cosmetic header nor the need to compile from source, those sound just fine to me.
Anyway: compare https://caddyserver.com/ to http://nginx.org/ and on the former you'll see way more marketing, logos, testimonials, quickstarts, etc etc ... looks way more like a product than an open-source free-software tool.
I always thought this was a weird trend for open source projects these days. I'm accustomed to debian, gnu make, nginx, apache, samba, cups ... useful tools with zero marketing and support. That's just how it used to work ... and frankly it still seems like it works better that way. A super modern website and easy-as-possible getting started stuff sets the wrong expectations in many many people who are not familiar with this world. They expect to do nothing and get a slick product / solution. They're drawn to the language they're familiar with from startups who get millions in funding and promise the world and then fizzle in a couple of years. That's not sustainable for open source projects.
Open source software is very useful and valuable and democratizing. Just the simplification of no per-user or per-machine or per-anything licensing adds a huge amount of value! The economies of scale of good quality open source software is super high. This stuff is really amazing and effective.
But the support does not scale. This is the one part you have to pay for with your own time. It could take years and years. That's the trade-off. You can't get it all for free, it's not possible.
