So I was thinking it'd be nice if I could hand people a copy of my DVD as a "Hey, look what you can do, and all you need is this" and after say a week or so it stops working... Timebombing it...

I know if they REALLY REALLY wanted in to it, it wouldn't be that hard, but you know, it'd still be nice if you could cripple it nicely, so that it would deter some people....

CodeGuru has a forum, specifically this thread, just for making trial software. Now, given that, I wouldn't know how you would go about aggregating it to your OSs. The only other way to do that is to include some trial key. I'm sure you can find those legally. Hope this helps