Good stuff!
I was heavily into big shows in the past, including 'points' shows. Now it's just a fun thing for me to hang out with fellow enthusiasts and chill out.
That wasn't the case before though as I would spend hours working on my show cars to win that trophy. I guess the most extensive event I ever attended was a Porsche 'points' show down in Atlanta with my 1995 993. I did win a class trophy and it was rewarding just like your thread states.
I also won a nice plaque at a Super Chevy event at the speedway in Bristol TN when I had an '87 Monte Carlo SS Aerocoupe.
Great memories for sure. Some pics of the 2 cars I mentioned below.

 

I've spent more on mods than I did for my car. Never won an award. Lol.

 

I decided to stop the car show thing about 8 years ago and have a shelf of trophies from local and regional events from my old Camaro. Just got to the point where I was tired of all the cleaning and detailing and then waiting around for the awards to be announced, which always seemed to drag out. Since then I enjoy the car cruises much more. Come when you want, stay as long as you'd like leave when you want. I park and sit with a bunch of friends and there's always a conversation going on. Very relaxing.
I'll still go to a car show with friends. I'll pay the entry fee (usually for a cause) but not enter it for judging. I just write "participant, no judging" across the windshield sign so the event sponsors know I paid. All this so I can leave when I want!