Ok Im a gay webmaster and I have been doing gay sites for 5 years. Personally I wish you guys would stay out of it and leave all the money to those of us already doing it but since thats not going to happen I'll answer some of your questions.
First of all you dont push your sites towards tops or bottoms. There are twink tops and twink bottoms. bear tops and bear bottoms. Really makes no difference. There are gay webmaster boards that help with newbies in the gay market and in fact I run one but I dont want to spam my board here. Not to hard to find though
