Not sure if you're still looking for opinions but I thought I'd give my two cents :)
I'm a cosmetologist and have been for the past 8 years! You have a nice face shape that you'd be able to pull off the Pob! I think it would look great on you!
The bad thing about short hair is you miss your long hair after a while and you can't pull it up when its that short....well not easily at least :) Long is easy to pull up whenever you need it but short hair is much easier to take care of. Plus going that short your hair will be very healthy since you cutting off all the ends which no matter how well you take care of your hair you're going to have dead ends.
Short hair means less shampoo, conditioner and less time blow drying too ;)