H.W.
Hi Magreen,
If it were me, I'd start with something easy to maintain and not too hugely different from what you've got going on now. Maybe a longish bob or blunt cut just at the length of your grown-out hair? This first cut doesn't have to be the be-all/end-all haircut. You might just need some time with it to decide where you want to go with it next, if you know what I mean. I *would* shy away from anything super-dramatic like a cropped or pixie cut, because it will take a while to grow back. With something longer, you've got hair to work with if you decide to go shorter or do something different later on.
Be clear with the haircutter if you want something that is low-maintenence, and be super clear about how much you want to do with your hair in the mornings after you wash it. If you just comb it and blow dry it, don't be afraid to tell them that. The reason is that you might not want it cut into a style you have to work on every morning.
Ask around, too, for a referral. I've discovered that I really like to work with people who A. like cutting hair and B. have been doing it a long time. For myself, I've discovered that more mature stylists tend to listen better and will not give you Joan Jett Choppy Ends when you are 7 months pregnant and just asked to have it "trimmed up". ( my true story...yikes!)
If you see a picture in a magazine of a haircut that you like, bring it in with you. Don't try to describe it too much, pics are better.
Highlighting is fine if you are willing to maintain getting it touched up every 6-8 weeks or so. And do some research on the chemicals, too. You could also ask about getting highlights/color that might wash out over time, so you don't have roots to deal with.
I usually tip my haircutter about 20%. It really depends on the service too. Awful? Don't leave a tip.
As for what to wear: they're going to put the cape on you anyway. I'd suggest something without a high collar, so hair doesn't get stuck in it and make your neck itch.
And yep, go for it! Even if it's a little change, sounds like you are ready for it!
Have fun!
H.