Section 20. In general, though, yes, you can run a contest or sweepstake.
I'd suggest you run your contest rules past legal first. There are considerations that vary state-to-state, considerations at the federal level (like you probably need to send the winner a W2-G or something), and considerations internationally (Canada has some strange rules - and they aren't the only ones). No point talking to humorless taxmen unnecessarily.
I didn't even think of the legal aspect. Can I put a note in the contest rule that say the winner is responsible for filing taxes on the prize?
Winners usually are responsible for ponying up the taxes. That does not, however, remove your obligation to report the winner to the US Govt (other nations may vary, but probably not) if the total winnings is over a threshold value. I'm gonna guess the cheapest iPad 2 is over that threshold, but IANAL.
On the plus side, contests really are the "kinds of things done everyday". A certified public accountant, a civil lawyer, a business tax preparer - any or all these folks should be able to ensure you're properly dotting the i's and crossing the t's. Pick up a phone book and call around!
Just be careful when performing contests and sweepstakes - there are rather specific laws when it comes to running them. That being said - most contests and sweepstakes by small app developers run under the radar, but all it takes is one overzealous entrant with a lawyer to take down your whole company if you do it wrong.
Here it states that Rhode Island is the only state that require me to file a legal statement if the reward is in excess of 500$. However the cheapest iPad2 is only 499$ so I believe I'm in the clear on that point.
It says the payee (me) only need to send a 1099-MISC form if the winnings is in excess of 600$, and again the iPad2 is only 499$, so I'm in the clear on this point aswell.
With this in mind I believe I am below all of the thresholds, do I need to file or report anything at all?
Here it states that Rhode Island is the only state that require me to file a legal statement if the reward is in excess of 500$. However the cheapest iPad2 is only 499$ so I believe I'm in the clear on that point.
It says the payee (me) only need to send a 1099-MISC form if the winnings is in excess of 600$, and again the iPad2 is only 499$, so I'm in the clear on this point aswell.
With this in mind I believe I am below all of the thresholds, do I need to file or report anything at all?