I am now creating only in Trainz Plus (which is also on your timeline). TRS22 is functionally the same as Trainz Plus for those who have both versions so I suppose it does not really matter between the two.
Of course this is only my opinion but TRS19 is now 4 years old (or more if you consider that it came out towards the end of 2018). For me the addition of Surveyor 2.0 in Trainz Plus is the real TRS19 killer. However, there are plenty of creators still working in T:ANE and even earlier versions.
Yes, but once you get over that curve... I now very rarely drop back into S1.0 and only for those few things that are not yet available in S2.0.
Now that I have the Trainz Plus beta also installed I am starting to experiment with its HD terrain feature, and a few other tweaks it also has. However, I still prefer the S1.0 Rulers because they are easier to spot and are not treated like other spline objects like the S2.0 rulers so you cannot accidentally move them or some other spline near them.