Why when I resize an image does it looks less sharp and poor quality?

I've been using Photoshop since CS3 and have never had thus problem before. I used to create websites using WordPress for clients and have created many different logo images without any issues. Now however I'm doing it for muself and I'm having problems when I resize the images for web use.
Here are a few examples. The first is a 1400x1400 image that I'm going to use for a podcast. iTunes requires this size and it looks good to my eye. When you look at the resized image however you'll see that it is not quite as sharp.
1400x1400 http://d.pr/i/SrtJ
300x300 http://d.pr/i/IqtI
Logo at http://safetydad.net
Twitter page http://twitter.com/thesafetydad
I've tried all different things to get it to look good at any size but no mater what when the image gets resized (especially by a CMS or Twitter) it looks like crap. I've tried saving as png, jpeg, flatteing before resizing, resizing the psd, saving as jpeg then resizing, using save for web option but no matter what it doesn't look right.
What am I doing wrong?

When you scale down, you will lose some of the sharpness because it is removing pixels from the image, and Photoshop is trying to figure out how to remove pixels, and reassemble the edges of the image.. As a result, when some of that shading is removed, it begins to blur. Make sure when scaling down an image (image - image size) that you set the resampling to bicubic sharper. This will help to reduce the blur from the pixel removal.
Also, you can go to filter - sharpen - unsharp mask - and work on bringing back some of the sharpness there as well.
For your twitter logo - I would make a separate logo for it, because the text is difficult to read over it. Sorry - just my opinion there.
You may have tried these things already - but if not - hopefully it helps
On the other note - I think you might be hyper-critical of the changes...

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