There is no comparing kites like the Widow Maker or Lam kites to off-the-shelf production kites. Different level stuff. But, good production kites like the Widow are more than enough for just about every kiter out there. For me, it's not just about how a kite flies, it's how it's built, who built it, how it looks, etc... With hand built kites, there's so much character in the wing, and they fly really awesome, too. If you appreciate all these things, it's worth $100+ more to go for a special kite that was built for you.
Your skill level doesn't really matter, as long as you're not crashing more than flying....