I have been running an 'info product' type business by e-mail & using Drop Box for some years (sports betting niche) It's been fine, I was not doing it to make $mega more as fun. We have a good social scene going on and all the members chat with each other and celebrate together when a big win is landed.
However, I now intend to run it is as a paid membership site.I am planning:
1. A simple sales page with a good offer. Probably going to offer 'First Month Free Trial'
2. If they take the 'First Month Free' offer, go to OTO for a 'Lifetime Membership' at $XX
3. Use Twitter as my main driver of traffic to the sales page
4. Once income generated then start Solo Ad campaigns
5. Turn members into affiliates
I already have over 50 members and I imagine 200 subscribers would be my limit. As the success depends on making money for them by recommending successful & profitable bets my plan is to drive monthly subscription costs up and keep total numbers down. So, I would start say at $10/month and aim to drive it up to $20, $30, $40. It's a very hungry market and if you can prove success then attracting members won't be hard plus I already have a rep and am quite well known (well my brand is)
I know you experts would probably split test and do all kinds of clever IM stuff.
I expect some would say give the first month for $1 or something to see if they really are buyers but I don't see that makes much difference.