My hair used to be long and now it's shoulder length. The bad thing about shoulder length is that it doesn't all go into a ponytail! The GOOD part is I like it far better than before and it's healthier because the ends used to be really dry. If you scroll down to the picture, that is the length of my hair now:

http://forums.teamestrogen.com/showthread.php?t=17190

When I ride, I wear a buff under my helmet and let it drape artfully down my back. I probably don't get style points but it keeps my hair from getting too dried out from the sun. When I take the buff off, my hair is usually soaked! I'll either leave it down (think drowned rat) or put it half up like Tom Cruise in Magnolia.

When I used to ride without the buff, even when my hair could go into a full ponytail, whispy bits would stick up out of my helmet. Hated it!

My opinion? Expensive hair cuts are always worth it and you should try it just to see. Worst case scenario is you don't like it and you grow it out. I think you looked good both ways but sometimes it's fun to experiment

And adorable animals. Good thing I don't live closer to you or I'd be finding a way to visit them SO cute!!!!