I think the board has two separate problems on is the dwindling number of members and the relative old age of the remaining members and the second is turning the members into cash flow. I think most of the good ideas have been mentioned to solve each problem.
In order to recruit new members we need advertising and the best advertising for this place is what worked initially quality content. But since this board already provides lots of written content i would suggest that. New members could be attracted through youtube and podcasting. I think youtube would be more expensive due to the higher production values but it would be trivial to monetize the videos and then you’re getting paid to advertise. My business runs a podcast as part of my advertising budget and it costs me about $500 a month for the editing, hosting and software my 2 one hour episodes. I’m my own star and do the writing and directing myself. To do it as cheaply as possible you could just read old columns and add in and intro, closing and a little bit of sound. From their you could follow the other podcast suggestion and do a chat show type episode either discussing the first show or doing more of the educated random banter we do here. That will cost more money because you’ll need writers and on air talent that will need to get paid more than a voice over guy from the first show. The youtube channel, the podcast and the message board then can be advertised on twitter and facebook with catchy clips or interesting conversations.
Both the old members and the new ones we’ll be drawing in will want to buy merchandise so that’s a great idea. I think membership tiers or buying titles are decent ideas but in general i think that bringing in more ad revenue is the way to go basically that would be by bringing in all the people above. I would also show ads to the members and give them something else for their direct support of the board. I know originally it was said that there was no preference from the owners of the board between members and guests because the membership fee just off set them not seeing ads. If that’s still true the revenue from the members could double by showing them ads and giving them a free coffee cup. Since it didn’t matter to the ownership and i don’t mind seeing ads i stopped paying when pay to post ended.
Lastly, keeping people here once we bring them in. I’m probably not the one to ask but I really hate avatars and threads with tons of photos and would come here less often at work if they were allowed simply because right now it doesn’t look too much different from work product. Updating the software and getting cleaner ads would be all I’d change. The board culture will move somewhat from the influx of new members but i wouldn’t force more change then that.