G'day Julian and Norm,
It's almost the exception rather than the rule for one of these old girls to sit level!

. A difference in diameter between the LH and RH rear tyres is the usual culprit. A difference in tyre pressure, tyre size or wear will do it. Even tyres that are supposedly the same size but different brands can do it. Long since gave up worrying about it. In theory I suppose you could level the deck by adjustment to compensate for a lean brought about by a difference in tyre size but I've never bothered with that either.
The axle adjustment might be playing a part too. The axle is supposed to be adjusted evenly at both LH and RH bearings so that the axle stays square in the machine when adjustments are made to the chain tension.
I can't agree that the Anniversary Machine is preferable from a design perspective. In fact I'm firmly a supporter of the older models. Easier to deal with, slightly simpler design, slightly more repairable. That's not to say there is anything wrong with the the Anniversary machines. But if I was in your position and I had a good ol' Tractor model in good nick I wouldn't be bothering with the Anniversary.
Play in the steering of the Tractor 8 might be able to be cured with adjustment. There is a large nut on the RH side (I think it's the RH side) of the lateral steering shaft. This nut adjusts the play out between the two gears and it has a tendency to work loose. I replace this nut with a nyloc if it's not already. Don't overtighten it - just enough to take up the play.
Cheers,