Snow is a great example. As a kid, snow was freedom from school, a sculpting medium, a sledding surface, a new landscape to explore...
As an adult, it mostly means tangled commutes and manual labor.
Granted, a gentle snowstorm can be pretty nice when you don't have work the next day, but it doesn't have the same magic it did.
Seconding Plex / Plexamp if the use case involves streaming remotely. Probably the easiest to get up and running for remote access.
I'm not sure about the capabilities of hosting on a Pi, but it should be straightforward to run a couple different apps in parallel to test and compare features (I'm currently doing exactly that with Plex and Jellyfin)