This is something I’ve been trying to do reliably for years. I can stream anything I want easily with VLC or even just Chrome itself but I can’t get subs to work. I was able to make it work for a long time using a Chrome app called “videostream” but it now no longer works correctly on my system. It’s a bit confusing to me but it kind of looks from what I have read that Plex can apparently handle this? Most references to the idea seem to be for later chromecast versions but mine’s a 1st gen I bought in 2014. Could I use Plex to stream local media with separate or embedded srt files to my chromecast ?
Yes, the transcoding is done on the fly automatically. Plex automatically transcodes any media that the client doesn’t natively support. Turning on burned in subtitles forces it to transcode to add them in.