the stubble look in picture #1 looks great on you. I'd stick with that or try shaving all the way. I like the stubble look on myself as well.
Don't be nervous about cutting with clippers for the first time. It is really easy, one guard all over. And worst case scenario if you do mess up just shave with a razor and you'll be back to what you have in picture #1 around a week.
Good luck.
