Right now, I think you are best off educating yourself by listening to your Pioneer and the Infinity speakers. Figure out what you like and dislike about them. If you still have the Bose, compare it too.
The difference between them (with the outlaw sub) and the Bose is substantial, why not enjoy it for awhile before you worry about upgrading again. I guess I like the idea of leaving room for upgrading later so you can experience the joy of improved sound more than once and next time (months or years from now) when you are listening to speakers, you'll have a much better foundation for evaluation.