Nope, you've only purchased it once.
Any user criteria that can be used by XenForo itself is allowed as criteria for entering a raffle. XenForo does not have a criteria for posts in X days, so that wouldn't be possible. Look at the criteria for User group promotions for what can be used as criteria for entering a raffle.
The points in that case is the XenForo phrase "points". I'll have to change that so it's a separate phrase and able to be modified on Monday.
If you mean.. can they enter more than once at one time?