[Stewart Bourke] "I was hoping for something that was a bit more 'dedicated' to playback control for multimedia productions (without the costs associated with some of the professional software I have seen out there)"
It's a niche market, with high performance and high reliability demands. There are some really great products in this space, but they all cost (and are worth) money.
I don't have a solution I could propose to you that wouldn't carry these costs, but I can describe a couple gotchas you should be aware of -- I know this doesn't answer your question, but hopefully it will be helpful.
The TripleHead presents itself to as a single, very wide monitor to the computer, so the system only treats it as one monitor (not three). Anything that attempts to use a full-screen mode will take over all three channels. Your playback software would need to effectively place your videos in 3 side-by-side windows on the second display.
A single laptop will probably struggle playing back three channels of high resolution video (or six channels, if you need to dissolve). Most professional systems would use one computer or playback device per output channel. You will need to make some tradeoffs -- highly compressed video files will be easier on the disk subsystem, but harder on the processor. Lightly compressed video files will be easier on the processor, but harder on the disks. Either could cause dropped frames.
What will you do when the movies aren't playing, or when you're transitioning from one movie to the next?
Finally, I always recommend running a redundant live backup of a playback system during a live event, so that a computer crash doesn't ruin your evening.
Good luck with your event!
Walter Soyka, Principal
Keen Live, Inc.
Presentation, Motion Graphics & Widescreen Design
RenderBreak: A Blog on Innovation in Production