The resized images are "jagged" looking because you are not actually resizing the image - you are just changing the amount of space that it shows in. The actually image is still 300px wide and the file size is the same, you are just showing it all in a smaller space.
I have created a Mod that will allow you to upload one large image and it will dynamically generate new images for the Product page, the Thumbs for the product listing pages, thumbnails for the shopping cart and also a popup for a detail - all from one large image. The dimensions for each are also configurable from within Admin.
This makes image management much easier and you do not have to worry about resizing in an application such as Photoshop. You would also not have to worry about creating and uploading multiple images.
Let me know if you are interested.
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