Go short or not?

[SpecialCircumstances]

I'm in need of some serious hair style advice!
Currently my hair is waist length and dyed ginger (looks natural!) my hair has always been fairly 'difficult' its very thick and wavy- not curly as each bit of hair seems to have it's own curl!
I'm just getting very fed up of it now- I have to wash it at night and it's still not dry in the mornings, I never wear it down as DS (9months) just grabs it and at work it's not practical to have it down (primary teacher) so it just gets shoved in a bun all day long.
The downsides to being short are: I'd have to style it every day. and I'm not sure it'll suit me- I have a fairly heavy jaw line and I'm worried it'll make me look more masculine!
Any advice? I feel stuck in such a rut after having DS and I'm desperate to feel more 'professional' and sorted before I go back to work!

I'd be cautious before going for anything too radical chop wise. As you say, if it's too short, you can't just bung it up and have done with it if you haven't got the time/inclination to faff about with it.

Could you have it in a mid-length bob that you could tussle up with your fingers (long enough to still be able to put it up if you wanted to) but that would mean it would dry quicker. Do you know what Kate Humble from Spring/Autumn/Winter Watch programme looks like? Would something like hers be a possibility?
It could work well just below jaw length, if you have a strong jaw line. I don't know how to link pics on here but I'm thinking mid-length, tousled bob? Of course DS could still grab hold of a good handful but unless you have it really short, he's probably going to be drawn to it like a little magnet for a while.

Oh, I like her hair! Mines less curly and more frizzy, but would a decent cut and some product help with that? maybe just long enough to pin up would be good!