I would like to propose thinking about more additional perks for site supporters (or, alternatively, less features for non-supporters). This might help in reaching the necessary number of paying players.
You might have a giant list of to-do features, but here are some of my random ideas:
Disable Zen mode or analysis mode for non-supporters
Blog articles or video lessons for members
Automatic game reviews for beginners (like, alternative “best moves” for each move by some bot? GnuGo’s --review option comes to my mind)
(From Another User.)
Now from this, I have to agree on most of it.
If we look at chess sites with supporters, you take a little away.
I would pay for something like this:
You take a game and a strong engine, (like Leela, or the paid deepzen or whatever) and allow it to judge every move in the game, based on win rates or a 1/10 scale. Now, you can make the whole analysis paid for (If you REALLY need money)
Or you can have something like:
-Quick (just quickly looking at anything 3 or lower, and giving 1-2 variations)
-In depth (Looking at anything ranked lower than 7, and giving 4-5 variations.)
-Extreme Analysis (going through EVERY move, and giving around 5+ variations)
I really like the thing with the articles, maybe also having some high dans on the site review some games they have played every once in awhile. Hell, maybe you could do an event, where you play high people if you donate. Just my thoughts on another user’s post.