Obsidian Vault Hygiene

Status: draft (2026-10-14). Written from one run: 74 venture-firm notes promoted from the vault root into vertical-toolkits/Venture-Capital-Firms/ (68 moved, 6 merged, all 126 inbound links still resolving). Generalize carefully as more note types go through it.

The layout you're working in

• The vault is /Users/mpstaton/content-md/lossless. Most top-level folders (Sources, vertical-toolkits, organizations, concepts, moc, …) are symlinks into the git-tracked lossless-monorepo/content/.
• The vault root itself is not under git. Loose root notes have no history. A bad edit or move there can't be undone, so back up first.
• Wikilinks use vault paths: Sources/… (capital S) even though the repo folder is content/sources/.
• Clicking a bare [[Name]] that resolves to nothing makes Obsidian create an empty note at the root. Many root files are 0-byte stubs created that way.

Procedure

1. Back up. cp -p every root .md you might touch (simplest: all of them) into /Users/mpstaton/content-md/_backups/<YYYY-MM-DD>-<task>/. Check the count matches.
2. Classify. Find candidates by name pattern and body keywords, then confirm the type against the CRM (orgType in the Lossless Twenty, read-only) and any event rosters. Sort into high / medium / low with a reason for each, and migrate only high. Hand medium to the operator (LPs, asset managers, accelerators and people with firm-like names live here).
3. Collision check. Search the whole vault, following symlinks: exact basename, the name with "Ventures/Capital/VC/Partners" stripped, and aliases: in frontmatter. If a typed note already exists, merge into it: carry over aliases, append any non-empty body under ***, then delete the root file. Never drop non-empty content.
4. Verify the URL. Take it from the CRM domain, an event roster, or a search confirmed against the firm's own site. If the name is ambiguous (several firms share it) or the site is dead, set no url and list the note.
5. OG fetch. Fetch the site directly. Fill only empty or missing og_* fields, drop placeholder values ("Home", "[]", a CMS default image), and set og_last_fetch. Add linkedin_url only when the firm's own site links it and the slug matches the firm. (The tidyverse/observers OpenGraph service does the same through opengraph.io when its API key is available.)
6. Frontmatter. Edit line by line so key order, quoting style and the body survive. Add only the missing standard keys for the type (see below). Keep any existing publish value; when it's absent, use false.
7. Move, then check that each moved basename is still unique in the vault. Bare links keep resolving only if it is. Rewrite to full vault paths: links to a name that's now ambiguous, links to a note renamed by a merge, and any path-qualified link to the old location. Escape the pipe (\|) inside table rows.
8. Verify and record. Re-scan every link to an affected name for breakage, and write a manifest (old path, new path, action, url, OG fetched yes/no) to the scratchpad.

Standard frontmatter by type

Other types (operating companies, LPs that aren't fund-of-funds, tools) have no settled folder yet. Ask before inventing one.

Anti-patterns

• Moving root notes without a backup.
• Creating a second note when a typed one exists under a slightly different name.
• Overwriting existing OG values, or keeping junk ones because "a field is a field".
• Guessing a domain from a firm name.
• Rewriting a whole frontmatter block, which reorders keys and changes quoting across files.
• Bulk-normalizing unrelated drift you notice along the way (mixed tags styles, typo'd keys). Note it and leave it.