

Rolling release doesn’t mean that no testing is done. All updated packages are tested by maintainers before being released into the official repository. A rolling release simply means that there are no individually marked OS versions and you always get the latest packages.
In contrast, take Debian for example. It uses a point release system with major named versions (e.g. Debian 13 “Trixie”), minor point releases (e.g. 13.1), and security and bugfix patches between those. New feature updates are released only between point releases, and breaking changes are only introduced between major versions. This allows the maintainers to practice a greater amount of care in testing that the packages work well together, but also means that new features are always held back to some extent. This does not happen in a rolling release system. All upstream changes are pulled, tested, and released, regardless of whether a breaking change is introduced.
By its nature, a rolling release distribution will require a greater amount of maintenance. If a package update requires manual intervention, it will be published on archlinux.org. For as long as I’ve been a Linux user, I’ve only seen one package update that made systems temporarily unbootable, and I was saved from that by being a Manjaro user at the time.
But, to answer the question, I usually update my home and work PCs (both Arch) about once every week or two, or as required by a new software or important security update.

If you have IPv4 addresses, I guarantee you’re behind at least one NAT gateway. What you need is a Tailscale subnet router, or something equivalent from another service.
In the most basic configuration, the Tailscale client facilitates communication (by using some UDP black magic fuckery) between one host it is running on and another host it is running on that are both connected to the same tailnet (the virtual network between Tailscale hosts). For this purpose, it uses addresses from the 100.64.0.0/10 “shared address space” subnet. These addresses will only be reachable from within your tailnet.
If you want an entire subnet (e.g. your LAN) to be accessible within your tailnet, you need to set up a subnet router. This involves configuring the Tailscale client on a device within the target subnet to advertise routes (
tailscale set --advertise-routes=192.168.1.0/24), allowing the host to advertise routes in the admin page (Machines -> … -> Edit routes), and configuring the Tailscale client on external hosts to accept advertised routes (tailscale set --accept-routes).If you want your servers to be accessible from anywhere on the internet, you’ll need Tailscale Funnel. I don’t use it personally, but it seems to work. Make sure you understand the risks and challenges involved with exposing a service to the public if you want to choose this route.