Why would multiple reboots make sense? I can accept three reboots triggering some condition that tries three times before it stops trying, but fifteen?
If you keep rebooting, you eventually may get those to load in the right order.
I'm wondering if you know wsl-vpnkit?
Anyway, had that confirmed by whoever is in charge of security and whatnot, as we have an internal StackOverflow clone and someone asking the same question was pointed to a PowerPoint presentation of dos and don'ts.
Now with WSL2 most pains I see are related to broken routing when also using VPNs on host. That is where that vpnkit tool shines.
Of course in win11 Microsoft decided to make the bridge hidden for some unknown reason, so good luck figuring it out...