I just received the three pocket fairing pouch from HD and it seems like the gap between the fairing and the windshield is too large. Has anyone else had this problem? I'm afraid to just close the gap by tightening I dont want to strip the screws.

 

Sounds like your windshield is not sitting in the fairing properly. Loosen it up and give it a wiggle, it should go.

 

Don't be in a hurry to close that gap. I did and the pouches scuffed my windshield. Looked like crap after only a couple of hundred miles of vibrating.
What I would look into trying the next time is to put a couple of silicon "feet" on the back of the pouches to protect the windshield.