Hi there M2J&L!
I'm going to jump in blindly and say that I am generally pretty clueless about hair, however, I couldn't but help notice that I am reasonably confident that your face shape and my face shape are fairly similar. High forehead, reasonably oval face with a slightly pointy chin (but not enough to make it heart shape - my chin is pointier though than yours!).
Now, if you agree and can see the similarity in face shapes, I can tell you that I'm discovering that what suits me, is to keep my hair above my shoulders in a longish bob. Even going as high up as close to jaw line, or just below my jaw is flattering.
I've been experimenting lately with having a fringe and am finding I really like it! For the first time in my life, when I wear my hair in a pony tail, my husband says "that suits you and looks stylish". A biggy I can tell you! In terms of maintenance, if you decide to do the bob type look, you will need to commit to getting it cut every six or so weeks (depending on how quickly your hair grows), after that it does lose its shape and it starts to go hay-wire.
If you are interested, go in and have a look at my personal profile, you'll find posts I've written regarding my own hairstyle and there are pictures of the results on there. My more recent WiW posts also feature my newer hairstyles with fringes (although I haven't posted many of these lately).
In terms of styling with littlies, it can be done with small children. The biggest thing is that you have to commit to it! (I have three boys and they are just under two years apart - so I know what you are saying.)
The trick for me is twofold - #1, when I wash (in general I do this every two - three days, except when obviously I swim or get sweaty!) I will properly blow dry my hair into place - not just leave it to air dry. #2, I then go over my hair using a GHD. That contraption has saved my life - I have the worst hair ever for kinks, cowlicks and general fine unrulyness! Then on the other days it is a matter of just using the GHD to smooth it out slightly in the morning, which literally takes about three minutes.
Blow-drying my fine, bob length hair only takes around 10 - 15 minutes and I figure that this is a good investment in myself. I will be honest and say that I've only really commited to properly "doing" my hair every single day these past six months or though. I feel so great every time I walk out the door though - I can't believe I used to let myself walk around with my hair all over the place!
Good luck and let us know what you come up with!