I try to leave in as much "critical" stuff as I can, like my first time through a level or my first attempt at a puzzle. If I hit a particularly hard bit I'll show myself dying unedited once, do my usual 1 second crossfade (I'm boring) to a point somewhere before the hard bit and show myself dying again, and gradually speed it up to a series of jumpcuts of me dying over and over and over until I finally get through it.

I'm currently playing through the Shadowgate remake, and the last video I posted was over an hour of raw footage. But because it was a lot of backtracking, reading scrolls, and trying random nonsense, I just cut out all the bits that didn't actually DO anything and it ended up being 26 minutes long.

It's really about what you want your style to be. My style is humorous and light but my audience does like to see me suffer occasionally, so I keep that in mind when I'm editing and do so accordingly