This is where my life-long dream of being an affiliate rep comes in to play.

If I were you, I would make an effort to find the site owner on a board first. If you can find them, PM with the specifics. This way you are addressing them with their board name, not "Hey Webmaster". Either way you do it, via board or email, make it as personal and detailed as possible. We've all received those letters from programs stating that they just visited my site and that my site and their program would mesh well. Tell them what it is about their site that makes you feel it would do a good job selling your sites. You know, something more than "Hey, I noticed you like naked chicks".
