I did sort of jump to the conclusion that there were no listen/spot checks involved...Mainly because I figured the OP would have mentioned something about unlucky reactive rolls along with his other bad rolls. If that is incorrect, then I still suggest killing the massive damage rule. It's crappy.
I am not a fan of spontaneous DM dice rolling. If a DM makes a habit of rolling specific skill checks then that is different. But if I've been rolling my own listen checks for the last 11 levels and suddenly I get hit with an death attack from behind with no roll, I am going to be seriously miffed at the DM when he goes 'I rolled the check for you....you failed'. My initial reaction is that the DM just wanted my character to be shanked. If I survived but took a lot of damage I'd roll with it and keep going. But if I actually had a character get killed from what seemed like DM fiat then I would be very sore about it. IMO DM fiat is called for when it will make the game more fun and interesting....but killing characters is neither fun nor interesting. Of course the danger is there that a character may get killed with an unlucky roll or whatnot, but you arent supposed to die as a result of a DMs direct intervention. 'Rocks fall from the ceiling, everyone roll up new characters' is the extreme example.
I tend to seperate my D&D into 2 categories....role-playing and roll-playing. And I don't tend to mix them together much....If we're in town and we're trying to get a meeting with Billy the powerful political figure, we're going to be in role-play mode. Probably walking around without our armor or weapons, or with them peace-tied or what have you. Basically we're not prepared to get into fights, and our goals are aimed towards the social achievements. If I'm in the lobby of this guys house and one of the bad guys walks in and stabs me, it's going to ruin any future consideration my character might have had for role-playing. Now, I'm always walking around everywhere armed to the teeth, and I stop caring about trying to role-play because I know the DM will just use that as a way to attack me when Im not prepared. It's not a matter of me trusting my DM or not, but an issue of me needing to realize that this particular DM has no qualms with using social setting vulnerabilities against us.
I realize that in the real world, its perfectly realistic for a gang to come shoot up your house if they know where you live. But in the DMD setting it just encourages a hack and slash mentality 24-7 when you screw with the PCs homebase....And apparently it encourages people to buy the stronghold builders guide
