How much time do you spend upgrading and fixing issues, if any? Rolling release has always scared me.

This has never been a problem for me. But when I'm running Debian I mostly run testing anyway. Also rarely a problem there.

On Arch I run sudo pacman -Syu almost every day.

You could run something like this to get a warning if there is anything that requires manual intervention: https://github.com/bradford-smith94/informant

I also run my laptop with Snapper: https://wiki.archlinux.org/index.php/snapper

I use a btrfs root volume with btrfs subvolumes instead of separate partitions. I have snapper setup with a pacman hook to take a snapshot before and after every pacman run. So worst case, if something goes horribly wrong, I can boot from an Arch install image into a previous snapshot and unbreak things.

I'm using Arch Linux on a VM since 2015. On that VM I host some services for personal projects, gitolite, Grafana, InfluxDB, wireguard and some self baked daemons (they are also deployed as Arch Linux package, it's not too hard and much cleaner and easier to deal with in the long run).

I update weekly to daily, but sometimes also a month goes by (e.g., if I'm on vacation or the like), never had an issue, never had any breakage. I reboot on kernel updates, downtime is a few seconds which I can deal with.

The VM is only single core, 4GB memory, 40 GB disk space - chugging along just fine.

Personally, I'd always feel safe and good with choosing either Arch Linux, Debian or Alpine Linux as VM/CT distribution (my underlying hypervisor would be Proxmox VE, which derives from Debian).

I do it weekly and it's fine for me. Of course evaluating first the nature of the upgrade. You know, Kernel or Arch base related upgrades specially. A different case for certain third-party packages or AUR ones, that usually they can be upgraded ASAP without friction.

I'm giving my personal experience here, of course depends on the case, but even kernel or Arch related upgrades that I do weekly are also smoothly.

I'm an Arch newbie (started using it in January this year). Never had any issues with rolling updates. A few times the update required manual intervention, but that was documented on the Arch website and took about 30 seconds to fix.

Historically, I've had more pains with upgrading on Ubuntu-based distros (but in all fairness I've been using them for much longer).

About 15 minutes every 2 months when my daughter updates her Arch desktop. All because of her Nvidia GTX480 (I know, she needs to inherit something newer already...) that has been deprecated from the official drivers so needs manual intervention.

The key factor is not really how much but how often. At least weekly I would say.

Also, the fewer AUR packages the better. Nothing too different from BSD packages vs ports.