Yup. It’s a shame they don’t natively support cloud solutions like iCloud, which is what leads to workarounds like syncthing. It’s because they want to push their paid cloud option instead. But I also recognize that iCloud and their cloud hosting isn’t self-hosted, so it wouldn’t really fit here.

Yeah, you always have to account for the wife factor. Same reason I’m using Plex instead of Jellyfin for my video hosting; I’d personally prefer Jellyfin, but the wife factor (really the mother-in-law factor, but whatever…) demands that it doesn’t require a ton of config on the user’s end. If the goal is to encourage use by your family, it can’t be fiddly or difficult to set up on their end.

It’s more work to set up, but a much easier experience if you have users who can’t remotely access Overseerr. You always have to account for the “mom factor” when hosting services; Will your mom be able to learn how to use it? My mom can use Discord, but good luck getting her to learn Tailscale to access my Overseerr remotely.