I use a frustration threshold. A lot of times, I’ve got a working solution, but it’s not “right”, so when that become frustrating enough, I build something.

A few examples

dotnet does not work on OpenBSD, so to run jellyfin (supported by the infuse app on the apple tv), I have to run Linux. I wonder if I can replicate the API somehow

calibre is quite nice, but I don’t use much of its capabilities. I could try to make a simpler system for my use cases.

And so on.