Plex

I would say no. The main benefit of having lossless audio is for archival and transcoding, neither of which matter in the context of streaming.

That being said if you are using Bluetooth headphones this will avoid possible double transcoding, and if you want the maximum quality no matter what then yeah consider lossless streaming.

Other than that? Not worth it. I have extremely high end electrostatic headphones and I still use YouTube Music. Modern codecs like Opus, AAC, and Vorbis are all perfectly capable of producing compressed audio that you cannot tell apart from the source.