"do matches seem fair and fun overall?"
Well races don't. There is a loophole that allows good players to deliberately loose on ladder to start a race with players of a lower skill level and easily walk away with a colossal crate.
I am fed up off seeing the leader of my race steam ahead several 100pts above everyone else. This is cheating the system.
The good news is that you could fix it quickly and easily. Why not group races by last seasons final ladder scores?
Then races would be 'fair and fun'
3 hours ago