TL;DR: The thing that broke my patience with raw WireGuard wasn't the first node or even the third — it was adding a VPS to a mesh that already had my home server and laptop talking to each other. Suddenly I'm juggling four private keys, four public keys, four AllowedIPs blocks, and th 📖 Reading time: ~27 min What's in this article I Needed a Private Sync Network for My Journals — So I Tried Both What Each Tool Actually Is (Without the Marketing Fluff) Setting Up Tailscale: The Fast Path Setting Up Headscale: Where It Gets Real Head-to-Head: Where Each One Actually Falls Down Which Journaling Apps Actually Pair Well With This Setup The Moment Headscale Won Me Over (And When It Lost) When to Pick What: Specific Scenarios I Needed a Private Sync Network for My Journals — So I Tried Both The thing that broke my patience with raw WireGuard wasn't the first node or even the third — it was adding a VPS to a mesh that already had my home server and laptop talking to each other.…