After reading (and responding) to a few of the threads here, I would like my time on the soapbox. ^.^
WW does need to "get up" with the times. I am not a "new kid", nor am I an "old-timer" - but I am a webmaster of some worth and I do manage a lot of sites and their servers. Some of the sites I work on are going through this same thing and the big question is, "How the #377 do we compete?"
You don't, you join or lead - but you never compete.
Engineer, develop and design a site that introduces your quality to the mainstream and actually uses (or abuses) the current "fads" to bring users over here.
IMHO Java is making headway into a lot of big time websites. I see more and more ecommerce solutions in Java - highly customizable and able to tweak your security with custom classes which is not readily understood by the amateur.
Front with Apache (of course) and you can have it running on most any hardware, from a (choke) Windows server to some high-speed RedHat box or even on a cloud server - virtualize for redundancy and let it grow.
Develop your new WW site in conjunction with this old site. Heavy on the resources (believe me, I know), but worth it in the long run. When ready to launch, subdomain the new one first for beta. Then... after your subscriptions reach a goal on that site, switch to the main domain and sub this existing site to wean off your die-hard oldtimers. You might lose some in the process... but here is my thought...
How can you cater to the Webmasters of the World without being a leader in the industry? How can you lure over the new up-and-coming webmasters if WW is so archaic?
Those are ultimately your questions.
Public (main) Site
1 - Recreate with a rich CMS (OpenCms is a good java solution, or go with some blog type of solution). Use CSS to offer "classic" and "new" views for your users - please them all, CSS is wonderful!
2 - Allow advertising to keep the Public Site viable.
3 - Keep your public forums without the ability to post links and moderated by senior users - let your community get involved in policing itself more
4 - Leverage twitter/facebook for announcing things like your Feedback Days, attendance in conventions and of course, any news written by staff (either volunteer or paid staff)
5 - Create layout for mobile devices (more and more webmasters are having to do this - so should their resource site!)
Subscription (private) Site
Follow the above... however...
1 - Use social media to "tease" about content (Twitter is awesome for this) which users will have to pay-for-the-privilege to see (either by hit, download or by subscription - both are pretty viable and easy to program for)
2 - Paid users have the option of removing advertising (or make that a feature of a paid subscription)
3 - Create tiered subscriptions for better privileges
---lowest level would just be able to view the private forums, but not post
---mid level can post to the private forums
---highest level would have the privilege of posting links as it would be assumed they are responsible individuals if they pay for that privilege and they won't want to waste their money, eh?
And of course, you need manpower. Writers who are worthy of being a WW writer! News writers for relevant events not just for WW, but for the industry as a whole. Imagery - for what tells a better story than a picture? There are sites now (Examiner.com, Mahalo.com) that actually pay users to contribute. Not that WW can do that, but look at their models - nothing strokes the ego of a web-denizen than seeing their article on the front page of a website they contribute to.... nothing.
And this leads to sectioning the site for different disciplines...
1 - Designer Section - all about the UI, browser differences, etc. things like CSS, Velocity, DHTML, XML, etc. (probably public or lowest level subscription)
2 - Developer Section - its all about the code man - for the programmers to duke it out over their language of choice. (mid level subscribers - definitely)
3 - Engineering Section - without the guts you can't make kaka - and here would be the admins who manage our servers as they tote their platforms and wail over shortcomings in technology.(would be the nitty gritty subscribers who dream up the future anyway)
This would make it a bit easier and not so intimidating to those who are secular and just want to participate in those kinds of discussions - or for the noobs you want to lure on over here. :)
Implement a search or BOTH articles & forum where users can find their information. Site search is just about as crucial as SEO. If someone cannot find something within 2 or 3 clicks, they go elsewhere. Search function should be displayed on the first page a user sees... no if-and-or butt about it.