Don't worry about how large the root ball is when transplanting. Some roots can be pruned without causing any problems for the trees.
I've decided to just plant it (sometime soon, when I'm not procrastinating/being-lazy). Main reason - I'd rather do it sooner than later, as they'll just get heavier. Also, I really dread the idea of re-potting these huge half-wine-barrels in the future, and I'd rather just have them in the ground and never have to deal with re-potting them ever again.
Now, the questions are...
I want to reduce the rootball so it is a little easier and lighter to plant (for things like lifting it in&out of the hole to adjust for height, positioning, etc.).
Is it safe to reduce the rootball back to the original, smaller 15gal pot size when I bought them? (the current half-wine-barrel is about 28-30gal I believe).
I don't even know if the roots have filled the entire barrels yet (it's been in them for almost 2 years) or if it is pot-bound.
I am guessing it isn't pot-bound yet, as it's only been 2 years and the barrels are quite big. Irdk though.
Also, timing (I'm in zone 10b, with no freezing winters)...
Is now/fall, or winter, or spring best to do this rootball-reduction by 50% and plant in ground?
Also, it still needs its' annual momiage/old-needle-removal and reduction of new branch tips (bifurcation)...
Can I do this around the same time as the rootball-reduction and planting in ground?
Or, should I do the momiage/pruning a season before, or after, the rootball-reduction and planting?
Which to do first - momiage/pruning or rootball-reduction/planting?