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I recently bought an iPad.

Most favorite free App: http://itunes.apple.com/us/app/flipboard-your-social-news/id358801284?mt=8

Games -
Mandatory first step (on any system I play games on):
I re-purchased the available ports of my beloved adventure games classics. On iOS these are currently Monkey Island 1+2, Broken Sword 1+2, Simon the Sorcerer 1+2, Beneath a Steel Sky, Inherit the Earth.

Second step:
I downloaded the helpful and very well-done Apps "AppShopper" and "Discovr Apps", checked the enormous library of original games and tried out more than 20 of them.

The first 5 real iOS games that I bought and got me hooked:
- Tiny Wings HD http://itunes.apple.com/us/app/tiny-wings/id417817520?mt=8
- Iron Horse http://itunes.apple.com/us/app/the-iron-horse/id364635736?mt=8
- Galcon Fusion http://itunes.apple.com/us/app/galcon-fusion/id419955867?mt=12
- Puerto Rico HD http://itunes.apple.com/us/app/puerto-rico-hd/id438437326?mt=8
- Epic Astro Story http://itunes.apple.com/us/app/epic-astro-story/id507409247?mt=8

Already my most favorite iOS developer:
Kairosoft from Tokyo, makers of Game Dev Story, Epic Astro Story and a few more stories. EAS is incredibly cute, deep and addictive. The next game I will get from these guys is Dungeon Village (no story this time).