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Selfhosted
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nginx is a beast, I haven't used Caddy. What I'd say to a newcomer is stick to the plan, just do it step by step. Don't go looking to build a 30-service massive 1000 line nginx file immediately. Start small.
Trying to do it all at once will make you go crazy, I made that mistake. Focus on one small thing at a time, slowly adding to your config, that'll make it easier. Also make backups, or better yet store the conf in a git directory or something so you can easily rollback. If you have one service running but adding a second breaks it and you want to take a break, it's a lot better rolling it back to a known good state rather than leaving it in a broken state.