My mainsheet has a stopper knot tied in it to where the boom goes just short of the spreader for downwind work, and then I've got maybe 3-5 more feet after that. I figure just to make it easy to grab the sheet if I need to when the boom is all the way out, as opposed to digging the stopper knot out of the block. This is for my end boom sheeting, of course. Also, the boom is set a few inches shy of the shroud, just in case there's a crash gybe, I don't want the boom taking abuse from the shroud. Of course, with end boom sheeting affixed to the backstay, there might be a fair amount of stress all around for crash gybes.
Then again, for some racing dinghies in big wind, I've seen videos around the gybing mark, and every gybe is a crash gybe. And every time I shudder as the boom whips around and stops short, that the whole rig is gonna come down....
If your mainsheet is too short, such that the boom stops actually feet from the shroud, I think that's bad, because on a broad reach or run, I think there's a higher chance of inadvertent gybing.
Brian