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Then there's me, reinstalling the OS because it's quicker than installing the three months' worth of updates I forgot about.
The main downside to a rolling release distro, with that much drift there's a good chance something will install that conflicts with something else, and nobody can really help because the only real way to replicate your install is to go back in time and do the same thing
Unless you are using NixOS
YMMV based on distro. IIRC OpenSUSE has upgrade "pathing" to reduce conflicts during long delays between updates. Geckolinux has an iso released 6 months ago and it will update to the latest OpenSUSE packages.
I honestly think Arch could handle 3 months as well as long as you update the keyring and read the update news from Arch.
NixOS rolling wouldn't give a damn but that's not really fair since it basically rebuilds the whole system :P
The biggest issue is not getting security updates for 3 months.