I like the first set better. This last attempt to me looks too fake. If I saw it outside of this post I would still think something was fishy about it. Just off first glance, the edge of the hair line is too perfect.
I have photoshop also, and I work with it a lot for work. I have a book that goes into detail about how to create the whole 5 o'clock shadow, but every time I tried it, I got the same results as yours for the most part. Never had one that looked natural enough. I may be too much of a perfectionist.
On the other hand, I may try the trial version of the software you used on the first set and see what kinda results I can get with it. I think your first set looks nice and I would never question the photo.