I haven't been posting long, so I can't say much about how posting/pictures have changed recently, but I have searched it for trip reports and I have been posting TR's over on Livetrails.com for the past year so I can speak when comparing with that site. As far as searchability, I would echo what others have said, its hard to find all TR's for a given trail, and I think this is in large part due to lack of consistency of TR format and titles; I like Livetrails with respect to this as every TR gets linked to a particular trail that is in the database and any user can add a new trail if it is not already in the database. It also has a map segment (as do the main trail sites in Washington and Oregon), where it is easy to scroll around to different regions/locations and click on trails that you are interested in. I also like that it is easy to add a GPS track and photos to each TR on Livetrails, as you can easily add from Facebook, Flickr, youtube or other online picture/video site accounts, or upload from your computer. That being said, that site is limited primarily to TR's while clubtread has many more useful discussions about a variety of topics, and there is a much broader information base on clubtread through previous postings, trail wiki's, and the current active user base. I think it may be useful for the IT department to look into adding similar features that other sites currently offer. Hope that adds some value to the conversation.
I haven't finished reading all the comments, but this struck me. There are many sites with better data presentation and resources than CT (think Trailforks, for biking) and individual apps competing for this audience. I find the main benefit of the forum specifically comes from reading another's TR of a trip that I have already done. This lets me measure a perspective of their experience against my own, and understand how they experienced a destination that I'm already familiar with, letting me gauge the worth of taking in that member's other experiences. The natural progression of this is that I spend time reading TRs of members who's experience I respect, even if I have never or never plan to visit their TRs destination. Someone new to the site isn't going to appreciate Karl's support, or Masiar's humor, or Arnold's..... humor, or Muskeeto's comprehensiveness, or Mazegirl's prolific-ness (if that's a word); the value of the cumulative contributions of active experienced members, not at a glance in any case.
If one can't get good directions and description of a destination, nor recent-ish data on conditions, or decent photo documentation of the challenges faced, or access to a community when you have questions (all mentioned here as concerns), one will look elsewhere.