Wow i was on a very similar setup last year software stack wise. I have a small pc i5gen 10 (eats way less than one might think due to the laptop hardware) proxmox on it running 2 debian vms one for home assistant the other for anything else pretty much that doesn’t require huge horsepower but through the weeks/months crashes and bugs i decided to move my media server to a separate box with native jellyfin install to make sure i have full advantage of the hardware acceleration. That machine is nixos but that’s a whole other story 😂.

I think constant iteration is the key/fun with self hosting. I can’t tell you a single thing on my not so long but very eventful journey that I regret. Maybe try to find what is actually “mission critical data” that you once setup you say i need this to be online and reliable etc so you can play more freely on a separate system be that a vm or anything. Oh and document everything you do will come handy 10000% i guess that’s the only thing I wish I could done better is finding a tool I like to document with. For me it’s like this: I start documenting then something annoying happens with the note taking app or it’s just bloated and I’ll unintentionally abandon the whole thing.

Anyway that’s me waffling 😂 Have fun and I’m happy to share all the little exp I have just give me a shout ✌🏽

I would recommend keeping NextCloud always-on - this way your devices will be able to take advantage of background syncing without needing to remember to WoL. This also makes it more useful for other guests, should you choose to share your instance.

Tailscale is a mesh VPN. And is this made in Obsidian?

Does it really worth yo keep Media Box off and turning on only when needed? I think you're just unnecessarily complicating things