I have watched some videos (including here) on spooling, and they all say to make sure that the line needs to come off the spool the same way it comes off the reel. So holding my rod as if I am casting (like in the video), it spins clockwise, so I make sure it is coming off the spool clockwise. I even double checked the video to make sure that is what they did. I may honestly be misunderstanding it, because what you are saying always seemed to make more sense to me, but I trusted the videos.
As for the line weight, my rod says between 10 and 20# test, so I figured 14 would be a good size to go. 20# seemed way to big.
Thanks for the help, being a noob can be tough, and this site has given me a lot of great information.