I say I'm going to try this with every new character I make. But I don't think I've actually followed through... except with a Breton necromancer who was around level 3 and I wasn't that attached to anyway (you guessed it: he fell off a cliff).
The problem with playing DiD for me is that there is often something "unfair" that happens to make me feel justified for a reload. The mouse will go funny in the middle of a fight. I do something stupid that my *character* wouldn't have done. I become victim of a kill anim.
Worse, though, are the times when the level scaling rears its ugly head. Around levels 5 or 6 and then again at level 15ish is where I start to see sudden jumps in difficulty. I may have been going along happily killing bandits and bandit thugs, and then I'll confront some new souped-up enemy which whomps me in one or two hits. I remember having that feeling in Oblivion, but interestingly enough Fallout 3 never seemed to strike me as notably difficult at particular levels.
The other thing that makes it hard for me to really start over with a new character is that I would need to do the same thing again, pretty much. Yeah, I can choose to avoid Riverwood, head West instead of North, or something like that, but if I *actually* played DiD I'd have a neverending string of characters who only made it to level 15 at best; I'd have to always go through the same guilds, do the same parts of the MQ, etc.
I think the only character I've done who made it above level 20 is my Imperial thief (still going strong around level 25).
What I do now is a "Dead is New Character" version. If I feel that the death *really* doesn't justify an immediate reload, I'll go back, make a hard save, then start one of the 20 or so other character concepts I have waiting. I just *start* the new character, get him out of Helgen. Then I can go back to the "dead" one if I want, or keep playing the new guy.
It makes it so there is a little penalty for dying, but not irreversible.
I'm quite sure that death because of glitches doesn't count! If the controls become unresponsive in the middle of the fight (though I never had that happen to me) and you die, you can reload.
And about the boring part....mmm, for me it's not. For example, I really liked what SENIOR CINCO was doing, playing a DiD stage 4 Vampire, so I started one too, and boy is it different(for me at least).
But this just depends on what you like, after all. Some people don't like the fact that they are somewhat forced to use their imagination in order to get a good RP feel. This is not a bad thing, we are different people with different wants and needs. It doesn't bother me. I use my imagination a lot, to fill in the gaps, even think up dialogue, stuff like that.