The kids will always feel pressure during games, whether it's 8U or 17U. They'll always have ups and downs. One week they hit a walk-off to win a tournament, and the next week they give up the game winning hit. I think the recruiting part is similar. Sometimes you have a great game in front of recruiters and sometimes you blow it. This forum has lots of stories about kids playing poorly while their dream school is watching.
But the games will (should) always be fun. The fun changes over the years. It's fun watching your boy become a man. It's fun watching him get better. It's fun to spend time with your son during long car rides. It's also more fun watching a well played game.
For the kids, most will get some amount of joy from mastering the game and performing at a high level. Winning will always be fun. Performing well at a showcase is fun. The biggest difference for them as they get older may be preparation. If they want to continue to have success, and have fun, they will have to put in the hard work between games.