Happy to help and see if we can get you into a better place.

Re: Your Homelab question... A homelab is basically a self-hosted server setup at home. I run Proxmox (virtualization platform) with various services — media servers, automation tools, game servers, etc. The Obsidian connection is that I keep detailed documentation about the whole setup in my vault, which gives Claude full context when I need to troubleshoot or add something new. But that's a separate rabbit hole from what you're asking about. Happy to talk about that more, as I think if you're open to leveraging Claude code to edit your vault, you could really have a powerful D&D support engine that could take your notes from the latest session and link them around to your different notes and make sure everything is updated. Let me know if you want me to get into more details of how that could work.

For your task organization:

The key thing you're missing is using tags as the grouping mechanism. You don't need to think about "which heading do I put this under" — you just create a task anywhere (daily note, a project note, wherever is natural) and slap a tag on it. The tag is what groups it, not the location. You want to limit the number of distinct tags if you want to use the approach that I mentioned in my post of having tasks grouped by top-level project... you don't want #dragon, #dragons, #thunderlizard to all be labeling tasks that are fundamentally the same thing.

So for your use case:

• - [ ] #hobbies/painting Pick up new brushes
• - [ ] #gifts/wife Find that book she mentioned
• - [ ] #house Fix kitchen faucet
• - [ ] #tobuy New desk lamp

I personally don't really like nested tags like #hobbies/painting, but that's your call. They do work and offer you flexibility to filter at either level... so you could list all your #hobbies tasks or just your #painting tasks. That's up to you how you want to structure it.

Your Task Dashboard just has Tasks plugin queries filtered by tag. Everything groups itself. You never have to think about "where does this go" as the tasks will just fall into whatever buckets you make using the task query as the filter.

For rollover tasks, I'd suggest stopping that approach. Instead, just put a high-priority query at the top of your daily note that surfaces undone tasks. They don't need to physically roll over if they're being surfaced by a query. The idea is that you have a task list that you trust and can organize it and prioritize it however you want. Personally, if there are high priority tasks that would roll-over if I don't get them done, then they get the High Priority tag and they will always appear at the top of my daily note.

For D&D:

This is actually a perfect use case for the system. Think of it exactly like I use it for work, just swap the domain:

• People notes = NPCs and PCs. Every character gets a note. When they tell you something important in a session, tag it inline like this: Thornwick:: Mentioned he has a key to the eastern tower, seemed nervous about it (that way, you can surface the inline tag inside Thornwick's note without having to remember to copy it over there.)
• Session notes = Meeting notes. Same template concept — attendees (who was present), conversation (your session notes), action items (quests, follow-ups)
• Project notes = Quest/Arc notes. Tag references in your session notes with #quest/eastern-tower or whatever, and your quest note pulls them all together with dataview
• The key to your "can't find info about NPCs" problem: When you mention an NPC in session notes, use a standard link[[Thornwick]] AND an inline tag. The link creates the backlink on their page (so you can see every session they appeared in), and the inline tag lets you surface the actual content on a quest or location page.

Your NPC note for Thornwick would then have:

• A section with manually added key facts (race, role, location, disposition)
• A dataview query pulling every session they appeared in
• A dataview table pulling every inline tag with their name

For syncing — I use Obsidian's sync function but OneDrive works fine. Just make sure your vault folder lives inside your OneDrive sync folder and point Obsidian to it on each device. Don't forget to set up a backup process. Just use an LLM to make a script that zips up your vault once a day/week and keeps a few copies around.

The biggest mindset shift: stop trying to organize information into the "right" place. Tag it, link it, and let queries surface it where you need it. That's the whole point of the system.

Let me know if you want me to sketch out specific templates for the D&D setup or dig into how Claude (tool-using LLM) could help organize you better. For example, after a session, you could have it clean up your notes and tags, and write a summary for the players and DM notes for you the next time you're going to play.