Should I cut my hair?

Don't cut it. You will miss those little bastards once they are gone, trust me! ¯\_(ツ)_/¯ Annnd remember you can make them fly on windy days and just feel glorious! xD https://64.media.tumblr.com/6904875836d8cd7602f3ced65d96d699/tumblr_inline_prcdijNYLt1qeoe34_500.gifv

Hair grows back. I suggest you cut it in a style that seems likeable to you and figure out during those few months of short hair if you like the change, how it ends up looking in both bad and good days, and if you miss your long hair afterwards. If you don't like short hair grow it back out. No damage in doing that as long as you don't place fire to your scalp or acid to ruin your hair cells that grows the strands out.

Look inside and ask yourself "Do I want a mane that will give thee ole razzle dazzle as I let the wind tickle and play with my hair or not?" And you will find your answer.

Also with long hair you can find a wizard and put a flourish enchantment on it so it always appears to be blowing in the wind.