I feel like that is 100% achievable! I don't see anything in the transformation that looks unrealistic. Increased softening of the jaw line shouldn't be a stretch at all, and everything else looks like basic cosmetics like with the eyebrows (it's always coming back to the eyebrows I feel like).
Don't be too self critical, the before picture doesn't look like a bad starting place at all to me. 🙂 I think you have a better starting shoulder and neck place than I do too by far. Just by the nature of the picture I took for the sake of the makeup it didn't really show that on mine. (Though I'm hopeful that I can drop a few inches of circumference on neck, since a lot of people have said they went down several inches on HRT with muscle loss. Supposedly proper posture which I need to work on more with yoga will help a lot too, pulling the neck up and muscles straighter therefore narrower.) (Also I cheated a bit with the makeup and wig. It's amazing how far a little foundation and lipstick goes, and hair of course is huge on presentation. Without, my before would be quite different.)