I have had a super short pixie type cut three separate times in my life and the main thing I have learned through my own experience is that you have to rock your style with confidence no matter what. There have been a bunch of times where I regretted having a short haircut and envied those with long hair. There were even times where I worried that I didn't look feminine enough and felt insecure. On the flip side, I find when I have longer hair I sometimes feel it is boring and wish for something short and more modern. But as I stated before, I have chopped a pixie cut three separate times now (each time from long hair!) so I have obviously evolved in my feelings about short cuts or else I wouldn't have revisited a short cut.

It can be annoying when friends and family give negative feedback on something like that and it creates doubt. But there is obviously a reason why you want to do it.

And it's your hair.
And it grows back.

I'm certainly not trying to convince anyone to do it or not do it. I'm just saying that I think you will decide to either do it or not do it and you should rock your decision with confidence. Even if people say the quintessential cringe-worthy, "What did you do to your hair?"

That being said, the pic is a little dark but it looks like you have really nice, strong eyebrows which would definitely look cool with a short cut! Also, you have a really nice, big smile and I think your features in general would stand out with a short cut. Also, you mentioned the thought of highlights. I don't think that would look bad at all, although I think rich, dark hair looks great in a short cut. Out of the four pics, my favorites are the second and third. I really like that choppy, brushed forward look with short hair. However, all these cuts are short, just styled differently. The first pic is just styled with the hair being pushed back.

Have you tried uploading your pic to any of the hair style try-on "studios", such as hairfinder.com or taaz.com (not affiliated) just to see how you might look with a really short cut?