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Different picture programs use different algorithms to resize/compress images. Some algorithms are more or less intelligent than others. My guess would be that the functions on the message board that try to resize automatically are pretty low on the evolution scale (likely pretty old and open source).
I'm looking into throwing something together that lays out some free (and non-free) tools that folks can use to resize & tweak their pictures. Any of the modern/current free tools out there should be much much better.
Here is Ricanbandit's taken through a simple "save for web" in Photoshop:
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