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Is it better to water the soil first or work dry?

I would say something inbetween. Soaking wet is hard to work on, bone dry is a risk for the tree not worth to take.

Yes. I should have said dry-ish.

So, I do prefere the slightly drier option. However it has happened that the substrate has been too wet for using chopsticks when I have a window for repotting. Then I just use water instead and wash the old soil off.

Will do that. Very good answer.
I think I still have to wait to see any new growth before doing a repot.
Although I've repotted it over the years pretty willy-nilly.