OK serious business post below:
1. Billing: Either you setup an account with a 3rd party biller (ccbill, epoch, verotel, etc) OR you setup your own merchant account (eventually both) along with NATS to run the Affiliate Program. In your case, since you do not want to go merchant account, I would suggest CCBill for their in-house Affiliate Program and Epoch (eventually) as a cascade (to capture those denied by CCBill). Less expense, less headaches but also less control. Plus there is the $1000 yearly fee for Visa and MasterCard. But still a good approach for starting your first site.
2. Hosting: You will need to find either a shared server (if your traffic is minimal) or a dedicated server (which is also good if you want to expand, add sites, use scripts to automate, etc).
3. Content: 20-30 videos to start the site. Put the old content in the Members Area as Bonus content (and to use as promo content to send out to affiliates). Being your first paysite I would not focus on upselling to yourself, micro-niching this or that. Get started, see where it goes, grow/expand/change as needed.
4. Updates: Depending on how many videos you have or plan to shoot weekly/monthly will determine how often you should update. If your content is limited you could also rotate content and updates to make it look fresh. But updating becomes a bigger issue the more traffic/Members you have so, to start, once or twice a week is fine.
5. Upsells/cross-sells: While it's a bit much to setup a whole network to cross-sell on your own you can certainly upsell other Sponsers and niches for your Members and find appropriate cross-sells (NOT pre-checked) for your Tour. Additional revenue you can pour into growing the site.
6. Pricing: One of my favorite axioms or principles is never de-value or under-appraise your own product. So $19.95 may be too low, meaning you could get more out of your customers than that. Try $29.95 or, if it's really out there stuff (as you indicated) then even try $39.95 to start. Those who are into the niche will pay for it and you can always test lower prices by dropping it $5 at a time. $19.95 may indeed be the 'sweet spot' for you but you won't know until you test it. Do NOT leave money on the table because you are unsure about the value of your hard work. OVER value it until reality makes you drop the prices.
7. Affiliates: See #1. But affiliates are important (yes, even today) because 100 people selling your content is always better than just you yourself selling it.
8. Advertising: Once you get rolling you may want to try some media buys (NOT 'buying traffic', as in click-through or re-directed bulk traffic). Meaning, finding sites IN YOUR NICHE you can contact and inquire about their banner or text link pricing. The smaller the niche the better bang for your buck you will get via advertising IF you find a good match for your content. (In other words, do not advertise a blowjob site on a lesbian site; advertise Asian schoolgirls on a Japanese site, etc.)
9. Members Area CMS: Depending on if you want to grow into one big site or open multiple sites down the road, a CMS (Content Management System) is a good idea. But programs like Elevated X or Porn CMS (both fine products) are relatively expensive for your first site. You may want to consider going custom or even a simple out-of-the-box solution. You really just need a way to display the content, release updates and display ads (upsells).
10. Design: I left this to last because you may end up testing many different designs. Depending on your budget (or if you have the skills to do it yourself) the cost for a simple, basic Tour is under $1000. Yes you can pay more but why if this is your first site? You can always try different designs/landing pages along the way. Don't be too precious about your first site, just get it live/able to accept Members ASAP. THEN you can tweak designs as you go along.
There are more but these basic principles should get you rolling and perhaps others can add to my list. Let's make this a real, useful business thread!
Best of luck either way, and good for you for taking on this new challenge!

