Should I change my do?

I want to try a new hair cut. In the past I`ve had medium-long hair and medium hair, but I`ve never gone short. I know that at about 2" my hair sticks up (mostly at the part). I`m considering going for a short look.

http://luna.spaceports.com/~flannel/flannel_leaves.jpg
this is pretty recent, my hair is 3" long and has a part.

http://www.hairboutique.com//tcmgallery/tcm0018.jpg
http://www.hairboutique.com//tcmgallery/tcm0027.jpg
These are looks that I am considering.

What does it take to maintain this kind of haircut? Do I have the right face shape to pull it off? If I don`t go with this look, what should I do?

Thanks for the advice!

- Dave Clipson