Hi Matt,
Welcome aboard! You must be keen to be starting out in the middle of winter. Don't worry I did the same thing a couple of years ago.
1) Regarding the deck grip, you can regrip a board. Check this thread:
www.seabreeze.com.au/forums/topic.asp?TOPIC_ID=372082) Is the mast track one of those that has a little button that allows it to move forwards and backwards? If so then pull the whole lot out (it usually screws in) and have a good look at how it's supposed to work.
If it's the newer type without a button, then just screw it in tighter. A picture of your setup would be good here to figure out what's going on.