Hey gmith. I hope you don't mind but I am going to post some of what I wrote you in email here for what it's worth.
.................
like I said earlier. I do not produce content. I am a programmer and I run a few free sites. With programming being my primary and the sites just being stuff I play with, Oh, I also collect domains ;p
With that said;
You can sell your content several ways. You could set up your own content store like at
http://voodoocontent.com/ or
http://adultlabs.com/.
You can partner up with a content broker who would sell the content for you and you both split the sale. I?m not sure at the moment who the big content brokers are these days. I have used
http://www.web-legal.com in the past, don?t know if they are still around.
You can sell your content directly using something like
http://clips4sale.com/, some folks claim they make pretty good bank on that.
Or you could try to do your own paysite. I have not built a paysite so I don?t know all the issues involved. However I think that is the hardest of all these to pull off successfully. I am not sure that everyone in the biz would agree with me on that one. There are people that did paysites before they did anything else and made it.
You can also do combinations of those. You can sell the content through a store while also selling it on something like clips4sale while also having your own pay/membership site.
.............
Adding this on, or you can also just make the content and then sell it on the boards. I have bought stuff directly from Dean just from thread posts in the past.
Research out some more. Decide what direction(s) you are going to attempt to go, put together a plan and do it
.