Looks like I missed the main activity period of this thread, but in my opinion DC is great in concept and general spirit. It just needs better tools/implementation.
Due to the many-possible-editors nature of the main non-discussion content pages, I think some form of Wiki makes tremendous amounts of sense. I don't see a WordPress or other such site being as effective as a straightforward Wiki. A Wiki meets all the needs I can really think of, aside from possibly marketing/aesthetic, for which you could perhaps just have a few still static pages, or a Wordpress-powered collection of pages, but even that seems unnecessary if you spend a little time prettying up your Wiki and theming it nicely. Wiki can be edited by anyone, if edits go awry it can be reverted, they can be multimedia-rich (including video, with plugins), have table of contents, glossary functionality, indexes and lists (e.g. list of all software by a particular contributor, list of all software in a particular category), and allow more focused discussion around a given page which could allow e.g. simple bug tracking and app-specific conversation that is more directly tied to the app's page (this makes most sense after a coding snack or other app is developed and made available, i.e. for long-term, ongoing bug discussion, feature requests, etc.
The forums as a community engagement tool are nice, but those and perhaps also the donation/user support system that is tied to them, need some new features which might suggest a new system entirely. I could call out some specific features like user mentions (e.g. @javajones, which improves engagement/stickiness), threaded conversations, easier topic splitting and referencing, better mobile support, better quoting functionality, better notifications, and more. Some of these are possible to implement with SMF, either with plugins or custom coding. A more radical but likely more effective solution would be to consider something like Discourse, which I've been very impressed with thus far (to be clear I am not running my own implementation at this time, this is just what I've seen from its feature set and testing it in its own discussion areas).
http://www.discourse.org/ There are other more SMF-like forums that have some of this capability built-in and might be less of a shock to the existing users, e.g. Burning Board
https://www.woltlab.com/wbb/ but I think ios a major software change is going to be made at all, it's worth considering something more forward-thinking like Discourse.
As for donations, my first question would be whether donations are really intended for (and at this time really do go toward) not just the site but also individual users. Do people toss a dollar or a 25 cents toward someone for a good, informative post? Do software authors, coding snack writers, etc. actually get many contributions? And if so are they coming from a variety of people, both old and new users, or is it more of a small-ish group of people who support *each other* and the money just kind of circles around? In other words is it more of a token gesture (no pun intended), or an actual, functional, useful part of the site? If the donations largely support the site itself, practically speaking, then perhaps it's best to make that clear or optimize better for that (although if it's working now as-is and there is a reasonable balance, perhaps it's already fairly optimal). If there is a desire to encourage more contribution to individual members, perhaps the site overhaul could help address that with plugins/add-ons to e.g. Discourse and the Wiki, and a better-branded, better-promoted (more "surfaced") donation/support system, something like Patreon/Subbable for example but oriented toward how things work here...
That's my 2 cents for now. Big change is scary and risky, but if you don't want DC to continue to just coast along as it has done for the past few years, then such change is worth strongly considering.
- Oshyan