Well I have some answers! First of all, thank you to all who replied... in hindsight, I was given some very sound advice.
My Dad was kind enough to take the head off tonight after work (I live a couple hours away from my tractor) and found the rings AND the valves to be shot! Turns out everything was the cause :)
We have a very trusty tractor mechanic replacing the valves and I'll be installing the new rings this week on my day off... as well as putting a set of new Firestones on it (Yippeeee!).
I hope this solves it all, because I'm out of time off before the big Almelund (MN) show.
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