Apologies again for the late response, but I figured it out. For anyone who stumbles upon this thread, here’s how a novice like myself solved my problem. I gave up on Nord’s Meshnet, but this was a simple fix and turned out better than I hoped: use the Pi-hole as a Tailscale exit node. Now my devices work better than ever, I get ad/tracker blocking 24/7, and I can use services remotely from my home network.
The official guide was very helpful, thank you for your patience.