I would recommend it. Speaking from personal experience, I trusted my VPN connection to remain on and self-heal. Thinking that cost me a strike against my ISP.
Now I know for a fact that if anything goes wrong with the VPN connection, all the containers that need it will need to restart before they have connectivity again and that can only happen after the VPN container restarts and passes healthcheck.
are we talking shooting up in an old abandoned factory bad, or “mom help I got my dick stuck in a fish.” bad?