If you are considering spending that much cash I would go for that WoZ on your wishlist.
I would only consider going CQ on a NGG if that was your holy grail pin and plan to never sell it because you'll probably be hard pressed to find a buyer that is willing to spend 5-6k or more on a CQ NGG. I'm going to assume that it would be even more like 8k+ for HEP quality NGG... you are talking about a machine that is better than NIB.
I'm a pin-noob as well and part of this hobby that I really enjoy is the hunt. One thing I've learned is patience...Nothing like scoring a wishlist pin for a really good price then doing what you can to fix it up. There is a plethora of knowledge and people willing to help out on this site. If you're willing to put in the time to do your research and ask for help, I think you'll find it's something that you can pick up on easily. In the end I find it much more rewarding than paying for a machine that's already been fixed up.
Of course HEP machines are in a league of their own and I'll probably never own one. At the very least its a good feeling knowing that you found a game for a damn good price and you made it play and look better than it probably ever had during it's lifetime. Plus you'll have a lot of good stories to tell