Well if you already know the game and the missions + quests involved, as well as the class you're playing with, you shouldn't have problems and shouldn't die.
As for the experience, well IDK exact numbers, but is kinda hard do all the quests, especially considering the Master's difficulty ones (like the one in Kourna were you're attacked by 3 mobs of 8 margonites, several times (Mirza's Last Stand me thinks)).
What I did and just to get my legendary survivor:
Created a Ranger in Prophecies, skipped Pre-Searing, got ran to LA, went to Cantha, did Sunspears in Cantha (more easy there with the level 20 henchmen in KC), got my heros, got max armor (still level 2), went back to Cantha and did the 3k experience quests in KC + Wajjun Bazaar, I think by then I was level 17 and about half the heros were level 20.
Then went back to Prophecies and stickied to main quests and missions, got level 20, and as soon as most of my heros were level 20 and I was ascended, did Consulate Docks and Vizunah Square, and started the storyline from both Factions and NF.
Got to Unwaking Waters, Ember Light Camp and Ruins of Morah capping useful elites in the way (EDA, BHA, BA, etc) and doing most quests (NF and Factions quests are well worth it) and I had about 800k experience. So I took 90k and started capping quick elites here and there, nothing over 10 minutes in my rough estimates. I think I capped around 110 elites in a few days. Boom, Legendary Survivor.
My best friends were: [Aegis], [Broad head arrow], [distracting shot], [ward against melee], [jagged bones] and [enfeebling blood].
I went Luxon side (ugh The Eternal Grove sucks), and got MoW in NF. Also got Master's in most missions (missed Tahnnakai for 31 seconds and Dunes of Despair requires me to do it again).
I think the lowest my health ever dropped was to 100 or so, when I aggroed 3 groups of Flesh Golems and some Mahgo Hydras, but that's all. Was also on danger in Silent Surf (a spot were 4 or so patrols of Outcasts + Dragons meet) and in NF when capping from the heket bosses in Yahtendi Canyons (were there are 4 bosses very near one of each other).
No farming, no Boxing, no elite tomes. If you see a mob wandering about just a few feet ahead of the completion of your objective, go kill it. You may aswell not believe on the non-boxing part, but I don't even have EotN
I didn't want to venture further as Kuuny can do big damage and Varesh brings me bitter memories. Oh yes, got to Abaddon's Mouth, saving the mission for when I get new armor and need to infuse it. And I'm sure someone more skilled can finish all campaigns without problems. So, gl

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EDIT: My other best friends are survivor insignias and pimp'd heros.