I'm so sorry to hear what a hard road it's been so far. Your post took me back to my first (horrible) two months of breastfeeding, and I totally relate to what you're going through. First, I just want to reiterate what mommal said about breastfeeding not being all-or-nothing. Every drop of your precious milk that your son gets is good and beneficial, whether it comes directly from your breasts or takes a detour into a bottle first. I know it can be hard to keep offering this gift to a baby that seems like he doesn't want to accept it, but you are the mama and you know it is what he needs- so just keep offering!
Regarding latch- after struggling to get my DD latched for months, I finally realized that it is not "me latching her" that we should be doing, so much as "me facilitating her latching." I had to ditch the head holding, the struggling to keep her hands out of the way, the propping her rigidly on a stiff pillow. I had to relax. I believe now that if I had done that from the beginning (and had a midwife who would have encouraged that), we would have avoided much of the pain and the feeling that breastfeeding was totally un-natural. Have you looked at all into biological nurturing, or laid-back breastfeeding? It encourages a baby-led, deep latch by letting your body support the baby and your baby find his way to the breast (with a little guidance from you.) It is in contrast to the "nipple to nose," pull the baby close when his mouth is open wide "method" of latching. You can check out this website for pictures and ideas.
Also, have faith that as his mouth gets bigger, it will be easier for him to keep a deep latch.
Are you doing anything to treat your damaged nipples?