I didn't compete in my youth, but what I gather from the book Why We Run by Bernd Heinrich, is that the biggest difference is that the whole CC vs. track thing isn't just a matter of the terrain, but how the events are scored. In CC, you are scored as a team and in track (except relays) you are scored individually. In CC, you commonly run on turf, so CC shoes are quite different from trail-running shoes, as they often have cleats.
As for the benefits of exercising on trails vs track:
- A huge break in the monotony
- Better scenery
- The varying terrain gives you all-around better exercise as you are constantly switching muscle groups
The consensus of most scientists is that running through the wilderness is what we evolved for. We certainly didn't evolve to run on tracks.
As for the cons: you have to watch out for bears, cougars, and NRA members out shootin' in the woods. :-) (So far, evolution has been on our side for surviving the first two.)
Regarding timing, once or twice a month get on the track or a flat paved course and do an all-out workout to gauge yourself and compare with others, and run in a 5K every few months. 4 out of 5 of your daily workouts ought to be slow-paced, and running on the trails actually helps you to slow down when you would otherwise be running a lot faster.