I would advise you to go with the 505, unless you need the extra portability that comes with the smaller screen of the 300. Other than that, 300 actually has fewer features than all other sonys, older or not. My understanding is that 300 was produced as a cheaper, "basic" device to be used either as a second device to carry around for experiences users, or as a cheaper choice to lure new ones.
You can also consult the reader matrix here on the wiki to see about specific features.
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