Anthony, I have to agree with Jaiem on this one. You really don't need to spend a lot right away until you get an idea what you really like, and then maybe up the quality of your fly fishing arsenal a bit.
I have a 10 wt rod w/ a 9/10 reel. I went about mid-or-the-line when I bought my outfit. I chose a 10 wt because I mainly wanted an outift I could easily battle a 30lb plus striper. Am I happy with my choice, yes, but I would prefer a 9 wt for 75% of my fly fishing. I've casted and borrowed some friend's 9 wt's and they are less of a strain to fish for an extended period. But, all this depends on what you plan on catching. If you are targeting schoolies and fish under 15 lbs, you probably could get away with a 8 wt. If you are targeting larger stripers and blues, with the possibility of fishing for falsies and bonito, you may want that 9 wt. If you are after the cows, a 10 wt may be the best choice. Again, it's all your preference. I second the Reddington's. Nice outift and guarenteed for life. They make a inexpensive combo too, I believe.
As for reels, you don't need to spend a lot. Plueger makes a nice, inexpensive reel If you want a better reel, which i would suggest for the bonito and larger stripers, you may want one with a disc drag. Personally, my number one line is an intermidiate shooting head, but I would suggest a standard weight forward intermediate as my first line and a weight forward sinking as my second line. I personally think you have limited area for a floating, but again, my opinion. Your ideal set-up will have at least 200 yards of 20# or 30# backing. With some of the new brids out, you can get even more on if you use them over dacron/micron.
Flys - You can't go wrong with various sized deceivers. Clousers work great as well. After that, you could go crazy. Buy a few different imitations of various epozy sand eels, poppers, crabs, squid, shrimp, etc.
Basket - Yes, make your own. Just buy the cone inserts and glue it in your basket. It keeps your fly line from tangling.
So, as you can see, you can go in several directions initially. You best bet may be a 9 wt. You'll always use it and you can always jump up to a 10 wt one day or go down to an 8 wt, but still use the 9 wt the most.
Good luck.
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