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You can probably skip Pilotwings. It was fine as a launch game, but it's lacking compared to the other installments in the series.

It also sounds like you could benefit from buying a Circle Pad Pro. It makes the system a bit larger, which should help with its comfort level. Portability might be affected, though.

As for games you would enjoy now, I recommend browsing the eShop. Most games have trailers and descriptions, and they tend to be pretty cheap.

If you're into pinball games, Zen Pinball has two fantastic tables (and two mediocre ones, but the good two are worth the price of admission alone).

Mutants Mudds was a surprisingly fun old-school 2D action-platformer. I sunk about six hours into it, and enjoyed most of them.

You'll have access to almost the entire DSiWare stuff too. 98% of it is dreck, of course, but it's got stuff like Cave Story, Dr. Mario, Tetris, and Rayman. I'm also planning on buying Dark Void Zero, Space Ace, and Zenonia. I'll let you know if they're worth it.

Virtual Console has some goodies in it too. The first two Mario games are there, and the third is probably coming soon. Gargoyle's Quest is a good pick up as well. Steer clear of Blaster Master though: it's nowhere near as good as the original.

Finally, make sure to give me your friend code.

You should generally steer clear of the 3D classics, though: the selections they've made so far aren't particularly stellar.