To your first point, I always wondered if there was a way to monetize the individual subs and allow moderators of these subs to somehow take a part of the cut. There are a million risks in this, and I assume the biggest fear would be that it would destroy a lot of the current culture and increase "MOD CONSPIRACY" fears; but it would still be interesting to test.
Regarding the subreddit finder, Pinterest has the perfect model for your first login where it asks you about your interests and subscribes you specifically to those types of things. Reddit should most certainly do the same thing as it did take me a while to get into the site, and the best day on Reddit was discovering that I could unsubscribe from the defaults I didn't care much for and find the communities I cared about.
My issue is most subreddit moderators are young guys who, for the first time in their life, have some small authority over a group of people and are total shitheads about it. They have no credentials other than having thought to make the subreddit before anyone, and have done nothing to deserve a cut of profits of anything. If I owned reddit, I wouldn't want these people to work for me.
This is essential-- mods already have way too much power, and are constantly found to be doing naughty things on a very reliable basis. Selling sidebar links, keeping funds from "charity drives", squashing certain domains, outright selling mod accounts to industry marketers (/r/android) and these are just the things we know about! Moderator powers need to be restricted with constant vigilance by the admins and community.
Adding the potential for monetary rewards will not move this problem in the correct direction.
Regarding the subreddit finder, Pinterest has the perfect model for your first login where it asks you about your interests and subscribes you specifically to those types of things. Reddit should most certainly do the same thing as it did take me a while to get into the site, and the best day on Reddit was discovering that I could unsubscribe from the defaults I didn't care much for and find the communities I cared about.