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Nice rebuild. Since you are more interested in development than media, I would reorder that list. Put Forgejo before Nextcloud: it is a single small container, trivially backed up (basically a directory plus a sqlite/postgres DB), and act_runner gives you CI to play with, which is a lot of fun for learning. Nextcloud is the opposite: the heaviest thing on your list and the most common cause of "why is my Pi4 swapping" posts. If what you mainly want is file sync and Obsidian notes, Syncthing plus a git repo (or Obsidian Livesync via CouchDB) covers 90% of it at a fraction of the resources.
Two practical notes for your exact setup, since both SSDs hang off one powered USB hub:
Keep Tailscale for SSH and expose nothing else publicly until Pi-hole and Forgejo are stable.