+1 for Jellyfin and Finamp but check out Audiobookshelf for podcasts and audiobooks. It even has regular checks for podcasts that you can set for rss feeds.

I can confirm that jellyfin continues playing until it is manually stopped. I once had it play for 12 hours straight without any interaction so I think it is fair to say there is no limit.

Ah, i see now. I use btrfs and the issue is with zfs.

I have been running my linux installs off of wd drives for years without any issues. Most of the devices I run are Asus laptops, maybe it is a Lenovo issue?

Do you have any suggestions for reputable security related websites?

You can use --accept-dns=false flag for tailscale on your parents pihole. That makes it ignore the tailscale dns settings and move on.

It is step 1 on tailscale pihole guide