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How good is the technology these days? Is there software that could pick up say, a youtube videos sound, and transcribe it with a reasonable degree of accuracy or does it all need to be trained to a "master voice"?

It really depends on the clarity of the voice and pronunciation. .Some voices work really well because people are eloquent speakers. Others are terrible because people smoosh words together, use slang, and these will require more frequent corrections. With a good voice and high quality audio it's worth it.

But you can also hire cheap labor to do it accurately, maybe even find someone on fiverr if the video is short enough.

I used to think I could transcribe interviews (for newspaper articles) with voice recognition software but I've been told it really has to be trained to a voice. I don't know if there is more expensive software that could transcribe general voices.

I had a co-worker who had a medical issue with one arm and used Dragon software. It worked pretty well for his voice, but he would send in stories to the office that had a fair number of errors that were slightly off from the right word. I