In my opinion (and past experience), the more incremental you can keep things the better.
That said, EE 3’s installer/updater is very much more robust and trouble free than EE 2’s. EE 2 made great strides in the later days (EE 2.7 plus updates were usually smooth sailing), but I have yet to encounter a failure of the EE 3 installer to do what it is supposed to do.
But why tempt fate? I would update EE 2 to the latest before the major update to EE 3.
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