Sorry for the latest in replying but it has been a busy day.
To respond in summary, the characters are:
Half-Orc Rogue/Fighter 5/5
Dragonborn Fighter/Barbarian 5/5
Dragonborn Sorcerer/Druid 5/5
High Elf Rogue/Cleric/Wizard 5/5/5 (barely made 5th in each, the others are half-way or better towards 6th in each already)
and a Tiefling Barbarian/Monk 5/5 (absent from session)
Yep, it is something the DM wanted to do. We are planing to make it well over 500,000 XP, and with the level cap at 20, he wanted to implement the old-school multiclassing system. While it seems OP, it really isn't too bad. We have a lot more options, but we're still limited to how many actions we can take and because the XP is split, generally have less HP and lower level abilities. Now, this is also because he runs a HARD game LOL!
For instance, in our session yesterday (minus the Tiefling, that player was absent and the character was otherwise engaged), we freed an archmage (little did we know at the time he was chaotic evil!!!) who we defeated (he teleported before dying), but my high elf died in the battle. Later on, the sorcerer/druid unleashed a barded devil while alone and died fighting that before the fighter/barbarian could save him (he killed the devil).
So, the remaining half-orc and dragonborn (already intending to see the Guardian Naga to raise the high-elf), left with the dead sorc/druid as well, took their retainers (4 guards and 1 orc, all in heavy armor), across the river to seek the naga. They were attacked by three green hags, who nearly toppled the boat, killing all the retainers and nearly drowning the half-orc in the process. The others killed one of the hags, and the others returned to the depths of the river with their five kills.
Since this was the day after the archmage fight, once on the other side and searching for the naga, the archmage returned--this time ready for battle. His Time Stop gave him five rounds (3 cones of cold and 2 lightning bolts). The fighter/barb was only 4 points from instant death, so unconscious and dying. The half-orc also went down, using relentless endurance (?) to have 1 HP. He made his deception check, fooling the archmage into believing he was dead as well. The DM rolled and the archmage proceeded to obliterate the fighter/barb with several rounds of magic missiles, laughing insanely the whole time.
The half-orc managed to sneak away, crawling through the high grass. Finally, when the archmage discovered this (the DM rolled his reaction), and he decided to spare him in return for releasing him from being stone. He told him to run, run little piggy, for the next time he would utterly destroy him as well! After the archmage left, the half-orc (who is LG) took the other two dead and eventually found the naga. The naga raised them, but there was nothing to do for the Fighter/Bard (the DM allowed the player to try by making some Con saves, but he failed...). The naga told the three survivors about a Druid to the north, who he believes might be able to reincarnate the Fighter/Bard if they can get there in time.
So, that was where we left off. Our next move is to warn the keep and the townspeople and flee. Now that the archmage is recovered, we can't beat him at this point. Hopefully we can reincarnate the fighter/barb, we'll see...
(Sorry for people who don't care for the tangent LOL

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At any rate, the real point to my starting all this was the issue that we were doing the assassinate wrong. The DM was allowing it in every encounter as long as the half-orc went first. Now that we are aware of the surprise condition, it isn't nearly as bad. He is still tough and deals good damage, but much closer to the other battlers.