I have been running wireguard for a couple of years now, with a DigitalOcean VPS setup as the main server.

One thing I've noticed, is that specific wg clients will occasionally lose their connection to the wireguard network, and I'll have to find some way to get to that machine and then a simple ping will re-establish it's connection, and I can access that system again.

Started using tailscale a few months ago, parallel to the wg network, and have never ran into that issue with the tailscale daemons. I started using ts, as my backend remote to the wg locked out systems to get wg working again, but ts has been so reliable vs straight wg, that I'm now making it my preferred connection preference.