Cut it or Keep it

I'm embarrassed to admit this but I still have not had my haircut "professionally" since November of last year.  Yes, I admit it, I've taken the kitchen scissors to my ends a few times.  Holy cow does it look like crap!  My hair is naturally curly and I straighten it about 90% of the time so I'm sure you can just imagine how dry and gross my ends are.  To make things worse, this is pretty nasty so skip this part if you don't want to gag... I've had dandruff for the past month.  I don't know why and I keep using Head and Shoulders but no luck.  I'm feel so unattractive these days.  My roots are a drab dark brown and the rest of my hair is a mousy brown... some might call it the ombre look! I call it too damn busy to get my bootie to the salon!
Well, not anymore! I'm in a new town, about to buy a new house (my first) and I have a babysitter now (thanks to my MIL).  This momma is gonna git her hair did asap!!  Question is, do I keep long or go with the short bob again?  And what do I do about the color?  Alright my friends, here are a few pics of me over the last 3 years.  Let me know what you think.  Keep in mind, I am 36, I have 2 small children and I am a stay-at-home mom.  Oh, and my husband has an important position with a very reputable financial investment company and I will be meeting the "big wigs" soon and their wives....if it matters.  Ok, here they are!

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LOOK UP!

Just now... no make-up!