Not to degrade the mention... I've done a lot of the same with Dokku on DO before. There's plugins for Let's Encrypt and some other bids. CDN, haven't worried about it too much, have used Cloudflare in front of a few sites, ymmv though.

Netlify is definitely on my todo/reading list... I just tore down my personal website and blog, with the intent of getting it running elsewhere. For my blog, I exported all the details into markdown files with front matter, but hadn't done anything to get it re-published anywhere. So, who knows.

I have a genuine interest in exploring a lot of this, but motivation + time have been limiting factors for me.