Presumably the skull/flag is supposed to be similar to a skull/crossbones - with us being the pirates (metaphorically) who're soon going to scare the pants of big comapnies (Ninty, Sony) by following a completely different - and much more independant - theme insofar as what we get for our console. Most other handhelds, bar the Zodiac, officially only get software that is directly licensed and costs; we get software that members of out community make. And remarkably, don't charge for.
Now, put yourselves in the shoes of someone who believes the only good way to get games is to put lots of money into making them and then charge more for their selling. What must it look like to see a community as close knit as this one is (at least, on its better days) producing especially good software and *not* charging for it? And I'm not talking about emulation, here - that, they might get shirty about (understandably, really), but the other stuff. We do actually have some particularly good free games, when it comes down to it.
Perhaps 2003 due to their being printed at a party happening then, or maybe its somehow related to the intended Euro Release of back then, which never happened. Who knows?