I would say take active steps to make it better, time is a fickle bitch and she won't fix your problems to a satisfactory degree potentially even after a very long time. ( In my opinion )
I think that it definitely will heal. You just have to be active about finding a process to repair the skin there. Are you using anything right now to help heal the scars?
The redness will fade, but the pitting is permanent unless you have scar revision treatment done. I can promise you that when the redness goes away the pits won't look nearly as bad.
The ice pick part may slowly get better over time (not too much), but like missamua said, the redness will fade quickly. And I would put retin A on ice pick scars. It thins and damages the skin. That's better for raised scars, not dents. hahaha