Marksman or Bowmaster

Also... if you're not laggy, I don't think you have any reason to die at squids past the first 10 minutes. After 10 minutes, you should realize that the only thing that does more than 150 damage to you is Goby Houses, Purple Squid lightning, and touch damage. Black squids are laughably weak. I hope you were talking about Purple Squids, but even so, you shouldn't die there unless you absolutely cannot keep your eyes open while you train. Even they do pathetic damage for their level. Spirit vikings do more than triple as much damage with their ranged attack. Dying at squids pretty much means you lag, you can't pay attention, you don't have enough HP to take a hit, or you suck at this game. Sorry to be the condescending one, but I can't believe (non-laggy) people die at squids.

Took me about an hour or so and 6-7 deaths to finally pound in that my HP always had to be above 1500.

It's a pretty common sense thing, but when previous monsters do 200-300 damage, you don't automatically do that right away. That's why I love Windraiders; a good transitional amount of touch/magic damage, not quite as high as real 'Ludi-syndrome' monsters but much more than the crap that V/H and the like dish out.