I cut off 12 inches off hair into the ever popular inverted bob. I also have decently curly hair, sounds like we pretty much have the same type. I don't regret it but I do miss my long hair just because I could do more with it. People tell me all the time how stylish it is, how it looks good on me, etc. But I will tell you the biggest problem I have, and it drives me nuts, is keeping it straight and curled under in the back. I had no problem doing it with long hair but short hair isn't the same. It tends to get wavy and I really have to work with it to keep it from flipping out. So it's not as quick as I thought it would be. It takes a little longer and time to actually style it. Before it was blow dry, run a curling iron over it, out the door. Now I have to stand with a mirror combing each section and really getting it good with hair spray to keep it from moving/flipping out. But again, I'm happy I did it and I really do like it but don't think it won't take work because it actually does.
The best piece of advice I can give you is to find a better hair stylist, especially if you're going to cut that much hair off. God forbid you take the plunge and do it and she does just an OK job. You really want it sharp and done really well or else you will be very unhappy. Don't feel bad. Sometimes it takes a while to find the right person and it's not like she's going to call you and ask "so where have you been?" Talk to your friends and get referrals to people to see until you've found just the right person.
PS - I use good quality products and I still have this problem. Also, I'm going to wear my hair like this for probably the next few months since I cut it all off anyway, but then I'm going to start growing it back out again.