Flash drives are a cool idea for having a copy of your most important stuff on you, but don’t make them your only copy. I’d also encrypt them if there’s sensitive data you’ll be carrying around in public.

A NAS with automatic backups really helps keep the library in one place if you’re juggling more than a couple of devices. Could make it out of a VM on your main PC, a repurposed old PC, or a dedicated machine. Spinning rust is usually fine for a digital library, maybe a SSD cache if you need extra performance. Don’t forget to periodically make a proper cold, offline, and perhaps offsite backup so you don’t lose your hard work.

Jellyfin, Syncthing, and Samba are what I’ve used to access my library and keep things in sync. I’ve been ripping discs before the rot sets in and downloading Youtube videos before they make it any harder to.

Also, grab a copy of Wikipedia for Kiwix (you can download specific parts with/without media to suit your needs and storage capacity).

As for the flash drive, I like to keep one on my keychain with Live ISOs, diagnostic utilities, and a small copy of Wikipedia in the unencrypted partition and a collection of photos, music, and documents in the encrypted partition.

I have about 60TB of storage on my Media server that I use for plex (I would recommend jellyfin for new users, but I have a lifetime premium). Now I would never pirate but if I did there’s Sonarr, Radarr, Lidarr and Jackett to make that all a click and go situation.

Recently started doing something similar at a larger order of magnitude. I would say Kiwix and RetroArch are a must. I learned Kodi is the most finicky piece of shit media program ever written (im being hyperbolic, I use it daily but wish that some settings were more intuitive). I also learned about FAT vs NTFS after spending days trying to download an 80gb file just to find that I needed to reformat the drive from FAT to NTFS. also don’t sleep on archive.org and the fact that you can use wget to mass download collections or search results.