Have you looked at getting different tips?
http://www.complyfoam.com/Look up Etymotic. I owned a pair of ER-4P and was very happy with them. I also have small ear canals and these worked very well for me. These used to be well under $200 a pair, but i just checked and for some reason the price seems to have gone way up.
My dad has a pair of Etymotic ER-6i which are within your budget. He's has no complaints. I'm not familiar with their newer models, but from my experience with this brand, you can't go wrong for the money. He also uses them almost daily around the house, while mowing and working outside, etc.... 2 years of what i'd consider abuse and they are still going strong.
I had a pair of Shures. I HATE their sound and will never own another pair.
I'm currently using a set of Ortofon e-Q7. These seem to be overkill for an ipod even when using Lossless. In this price range, it seems to me that the ipod becomes the limiting factor in sound quality. Ortofon makes a cheaper version, the e-q5. Might be able to find a used pair close to your budget.
These are just the IEMs that have personal experience with. Can't comment on other brands.