I've made a lot of "interesting" decisions and some things were silly, some things worked out, some things I needed to fix.
I've been self-hosting for a long time. Before commodity virtualization (let alone containers)... As technology improves, one must adapt and that often involves rebuilding, migrating, retiring software.
My only regret is the data I've lost from insufficient backups. Everything else is part of the fun, part of the experience.