Hun, that sound very stressful for you I also agree with Marcellus about seeing another LC or calling the ABA. It sounds to me like there might be something going on like a tongue-tie which is affecting his attachment. These can be really difficult to pick up sometimes, so you sometimes need to see a tongue-tie specialist. Depending on where you live, the ABA will probably be able to help you with a list of LCs nearby who can help you further with this.

In the meantime, have you tried Baby Led Attachment (BLA). This often works for mums who can't get attachment working using the mother led techniques which are most often used in hospitals. BLA works on a baby's natural instincts - babies can find the nipple and attach themselves using just their instincts, from birth, and this instinct lasts for months after birth. Usually mums have most success with this when are reclined in a chair comfortably, and have the baby on their chest skin to skin (although it is ok to wear a top that doesn't get in the way if you are more comfortable that way). Then you gently support the baby as he makes his own way to one side and attaches. There is more information and some pictures here - Australian Breastfeeding Association - Baby-led attachment. This is certainly worth trying as it is mostly more successful. If you are still unable to get him attached properly than a visit to a good LC to rule out tongue-tie or other physical problems is a good idea.

Best of luck hun