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

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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.…