I was never able to break five without going to the Valley of the Fallen first.
That's a decent thing, tho... that means you can wear the Armor of the Order either just before or sometime during Bonegrinder's cave, depending upon whether or not you scored a couple of lesser known skellies and such.
I finally made it, level 5 with one skeleton. After I killed the necromancer, I started to kill all the skellies I could find. By my good fortune, I killed what seems to be the last skeleton and Rynn's body glowed.