[CalebD]

Dudes. There is a bit of a catch-22 going on with what you are trying to do - bust into sailing on other peoples boats without much sailing experience. You may get lucky and find someone willing to take you out but that may mean hanging around those 'smug' places while trying to insinuate yourself on some boat owner.
The catch-22 is that you will find it much easier to meet people who own boats if you happen to own one yourself. When I was your age I was sailing on Sunfish, various day sailors and even windsurfers that brought me into contact with folks who sometimes owned bigger boats. Frankly, back then I did not really want to hang out with the older guys with bigger boats even if they could have taught me something about sailing.
Get a Sunfish, old Laser or catamaran or any small day sailor or even learn to windsurf. The smaller the boat the better as the overall cost is much cheaper. For windsurfing I would suggest taking some lessons. Once you learn to sail you will meet people out on the water or on the beach who might consider you as potential crew.
Another angle is to get your launch operators license (OUPV CG license) and drive a launch boat for a local club. You will still meet the folks with the big boats this way and have a job to boot.
It kinda sucks when you are young and want to do everything but can't because it cost way more then you can afford. I am only suggesting that there are smaller boats that you can afford and other avenues towards your goal then hanging around a club you are not a member of, wearing a blazer or Izod shirt you hate.
There are many down to earth small sailboat (< 33') owners out there but the bigger the boat the less it leaves its dock and the more expensive it is. It's complicated; that's all. It is easier when you have your own boat (however small).
Good luck guys.