Sponsorship: Homely Girl Seeks LTR

I once offered Gary Fisher a one year supply of home made cookies if he would loan me a bike for a 24 hour race. I later made the same offer to the guys at Surly. Gary never got back to me. Surly kindly explained that the size of their company prevented them from getting involved in this kind of "sponsorship". When turning me down they showed a genuine interest in my endeavors and I have the utmost respect for that.
At the restaurant, we get dozens of requests for donations to every charity, private school and softball team. In the end the only thing that we can do is set a budget and try and pinpoint those events or people that we have the most connection to. It is all about community.
I can only imagine what it is like for the people who have the task of sorting through the sponsorship requests for companies like Gary Fisher. Every Sport level rider with a Norba license and an email account must be taking a stab at the schwag wagon.
" Dude, I have been tearing up the local wednesday night races and I am getting set to do some big races next year. It would be totally sweet if you could hook me up 'cuz when I start bagging those podiums I could be representin' y'all. "
Reading enough of those would make you feel a certain disdain for everyone with their greedy little grease stained hands outstretched. Aside from the above mentioned occasions I have avoided the whole sponsorship thing for fear of being part of the problem. With the Great Divide Project underway I have decided to give my position another look.
A friend of mine who has spent a lifetime in the bike industry has been supportive of my situation by telling a few of his friends that they should help me out. I feel a little like a homely girl with a good personality getting set up on a date. As much as I may want the end result I don't feel great about the position it puts me in. I know that there is free stuff out there and if it doesn't go to me it will go to somebody else. I just feel disconnected from the whole process.
I commute by bike, I race bikes, I have organized rides/races, I vacation on bikes, I support my Local Bike Shop, I always give a nod or wave to other cyclists on the road; but I feel like a lurker in the bike community. I ride alone, I bike at odd hours, I have never belonged to a club or team. This has mostly been a by-product of my work schedule and my interest in doing types of rides other people aren't interested in. I have a feeling things are changing for me. I have been meeting new bike people, people who don't scoff at Carhart shorts, fenders or day long rides on dirt roads.
I would like to gain the perks of being part of the bike community through a natural process. Without having to be pushy. I am going to make some attempts to break out of my shell by connecting with companies that I feel some connection to. I don't want to take the goods and run, I want to feel that something can be gained for everyone involved.