The new generation planes are great, and the old planes of the 80s and earlier can't hope to match, but there are many good pieces of 'old iron' out there that can get you started for WAY less. You can pick up a #4, $5, and a #60-1/2 for less than the price of one Veritas or Lie Nielsen plane.
I have four Stanley #5s that I picked up at yard sales or off CL and didn't pay more than $50 for any one of them, and that one was almost like new and still in the original box.
I found a #7 on eBay that I won the bid on for $75, it's like new. Not a museum piece but that's not what I want it for, I want a good worker, not something that collects dust or is under glass.
I made a rabbit plane from a chuck of 12/4 oak and a 3/8" Allen wrench became the blade. Of all these planes I only bought a couple new, and that was 30 years ago, except for the Veritas shoulder plane. At an estate sale earlier this year, my sister found a Veritas Apron Plane and texted me asking if I was interested. I said yes and I would go as high as $40 since it came with a spare blade and looked to be barely used. She was able to pick it up for the $40 and I added it to my stable of planes. That plane is still in production and sells for $124, plus another $30 for the second blade, so I think I got a good deal.
My point is you can good work with some old planes to start, and keep your tool budget under control. Later when you 'need' that $300 plane go get it. You'll have a better understanding of what you need and the original purchase won't go to waste.
If you want to read up on the old Stanley planes, check out Pat's web site which covers every plane Stanley ever made.
http://www.supertool.com/StanleyBG/stan0a.html