Suggestion:
I'd say to hold off on everything but the iPhone. Your going to spend alot of time on the iPhone and the cash that you would spend on getting a PSP or DS can go toward getting some incredible apps and games on iTunes.
You have a PS3 already so you have the best gaming console on the market. Natal is going to be a joke just like every peripheral xbox has come out with so far. Plus you know it's going to take a lot of time to tweak it and work out the bugs. Seriously it took 8 month's to get netflix party system that was promised day one, another 11 month's to get 1 vs 100 which was promised on day one and still 2 years later people still get dropped from party chat. So take it with a grain of salt when microsoft hypes up anything. If you have the extra cash then picking up a 360 isn't a terrible idea. There's a few solid IP's on it like Mass Effect, Gears of War and the Fable franchise. Since your a PS3 owner I don't need to tell you that the games will look the exact same. However some will look better on the PS3 because of a little thing Xbox owners know little about called "True 1080p" which you can't get on xbox360. So if you see a game on both systems look at the setup info on the back. Because 50% of the time the same resolution will be on both but the other 50% the PS3 title with have the best available resolution. Right now it' a tough call. Two years ago I would have said by a 360 hands down. But right now Microsoft has put all their eggs into natal an have lost focus of creating solid exclusives with Halo Reach and Fable 3 being the only well backed exclusives. We're at the point where the exclusive game has changed. This year Sony has 26 and counting exclusives slated by Nov. and Microsoft only has 8. So you'd really only be buying a 360 for one of those 8 games since you can get the rest and more on your existing console.
As for the DS and PSP. Your dad is 100% right in his common sense. With the failure (epic) of the PSPgo and the announcement of the 3DS it's going to be a busy year for portable gaming systems. It's still underground but Sony has announced some improvements for the next system. One of which is a touch screen and accelerometer just like the iPhone. But, Nintendo has slated this new DS for the 4th quarter. Which to tell you from someone that's been in the industry awhile. It's BS… The technology that will be implemented in the 3DS isn't even complete. Unless there's some serious hustle going on further behind the scene's then it's going to be a long shot we'll see it sometime this year. Possibly 2nd quarter of 2011.
So my answer for you would be to get the iPhone spend a little time with it as far as games, music, movies, apps. There's a lot going on and it will definitely occupy your time and need for something new and cool. If after that you decide you still want a little more of a straight lined prtable gaming system then check out your local retailer. Look at all the NDS games and PSP games. See which one has a better selection that suites you. Then base your decision from that. If you go PSP then don't buy the PSPgo, buy the 3000. If you lean more toward the NDS then get the NDSxl because it's going to be at least a year before the 3DS or new PSP will be out. Hope it helps and have fun with your new toys.
Oh, almost forgot. As far as the iPad goes your going to want to wait. The first run will only have wi-fi and the second run will have 3g for only a $17 a month fee. Which is friggin awesome for anyone who pays for roaming net as it is. Also the first run has no USB, webcam or ability to multi-task. The second run will have all of these. Talk to anyon who has ever purchased he first run of anything Apple will tell you how mad they were 6 month's later when he next gen model came out with twice the features at half the price. So hold off on the iPad for now and you won't regret it in the future.

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