I'm in a similar boat.
Have a 2015 S that I will have had for 6 years this May.
The car has been rock solid, but I'm ready for something else (this is the longest I have ever owned the same car by a long shot).
I know for sure I would want to move to the R (if I decide to stay in the Golf family)...but the big question for me is keep the stick, or succumb to flappy paddles....
You will miss the 3rd pedal sometimes... only until you rip through a few gears in the DSG. It... is... that... good...
This is my first "Automatic" car. I've owned at least 5 other manual tranny cars. This is the only auto I'd buy, and I wouldn't have it any other way.
Key points are - you don't have to worry about upgrading your clutch if you want to make more power, and the car is just so much faster.