I actually think you should get the first version. Consider this:
Amazon.com sells the 16gb for $269 WITH shipping and taxes
Apple charges $299 plus about $20 for taxes, then add shipping if you're ordering online.
Amazon (1st gen new): $270
Apple (2nd gen new): >$320
What are you getting for $50 more dollars: Longer battery, external speaker, dedicated volume control. Those are all nice features, but from personal use of my own Touch, I'd say the new ones aren't worth $50 more.
If you want to save even more money, you could buy the 1st gen Touch used from amazon for about $225 (total) or refurbished from apple for $250 (total)
hope that helps...