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A few game recommendations:
Crisis Core - If you enjoyed FF7
Final Fantasy Tactics: War of the Lions - If you missed this on PS1
Jeanne D'Arc - I haven't played this yet, it's next on my list. Great reviews and I have some friends who really enjoyed it

The PSP 3000 might be worth waiting for as they will come with a 4 GB memory card (vs. the current PSP 2000 bundles that come with a 1 GB card).

Here are some details on the new PSP 3000 bundle:
http://blog.us.playstation.com/2008/08/20/live-from-leipzig-north-american-hardware-announcements/

Overall, I would recommend getting a PSP if there are enough games out there now that interest you. I held off from buying one until just recently because of lack of games that interested me. I did end up buying one a few months back and have been enjoying it since. I use it for both gaming and it's media capabilities.

As for the PSP2, I doubt we'll see it in 2009.