lot a good stuff in this thread, got a good laugh or two!
never skip litany flagging on a tr or any toon. those quests give such good xp that you can do them to gain the sigil piece and not get any extra pieces and turn them in and still be fine next life as you do it again! i always have a completed sigil while STILL farming those quests for xp on all my trs, i used to bank pieces but find it completely unnecessary as the xp is too good, you can skip gh and vale on single trs with necro 4 farming (double trs still need to hit the boring quests tho).
with that said, playstyle is a huge factor to the OP, 350hp is fine if you are amazing and keeping yourself alive. you wont get 1 shot with 350hp (base, not buffed) so as long as you run away when you are hit with a big spell and umd heal up, you will die less than the 800hp barbarian every time cause he has no evasion and cant umd heal scrolls.
also monks are front line melee, mine can reach 721hp and tank everything in the game as a human (not wf or dorf) so potential is much higher for those races. highest hp goes barb > fighter > monk simply cause fighters and monks get so many extra feats and those 22hp toughnesses add up. paladins can never reach monk hp so id def put monk at front line melee if built right. /endderail
also to the OP, your caster is more important than your healer. a good caster makes sure the cleric ends each shrining sessions with 80% or more sp (if healbot of course) cause a good caster cc's EVERYTHING! before the melee even gets near it or can get hit from it. so make good friends with good casters and your epic life will be a breeze. Also, a great healer will keep you alive with 250hp as well cause there are some good healers out there that can keep any squishy rogue up! so make some friends and epic with them.