My ideas for this are:
Add a "random" button, that brings you to a random trip report. Sometimes at lunch I like to read a few trip reports and this would make that a bit more fun. I read all of the trip reports, so a random one is a good way to get some old trip report to pop up from years past. An additional idea here would be to allow specifying a range of dates to select it between. Or a range of months (any year), so you could grab a random summer trip, or winter, for example.
If we don't get a random button, then how about having the "page" a drop down so that a user could go back 20, 30, or 100 pages in the results. The old forum did this, but the latest trip report tool did not and you could only go like 2 pages at a time, which meant it would take forever to go back like 50 pages.
Allow seeing 100 trip reports per page in the results.
Some trip reports have no "route" defined for them, which means that there is no link to get to those trips in the trip report search (well, now there is no trip report search anymore anyway). It should be possible to get all of the reports that fall into this category via a script...perhaps when the trip report search comes back again.
Restore images to trip reports that have them missing. I know you've done this a few times manually using the wayback machine. It should be possible to automate this and restore most/all images in the old trip reports?
To avoid losing pictures in the future, perhaps the software could be updated to make a copy of any linked photos in future trip reports so that the images still displace on CC when whatever random blog or website it is linked to inevitably disappears. Here is a random example of pictures linked to a now defunct website:
