Honey, get your ob-gyn to recommend you talk to a lactation consultant. It sounds like the wide latch is right, but maybe there is something else that she can see happening that will help. I hate to say it, but I think my nipples hurt for the whole first six months of nursing, and only determination saw it through. It was worth it but I would not recommend pain to the extent of tears to someone over nursing.
There are a couple of other things you can do. Medela makes a really high-grade lanolin that comes in a tube, I think it is called PurLan 100. It is very soothing to the nipples. Also, if you take plain old Lipton tea, and make a really, really thick concentrate of it (like, put six teabags into a cup of boiling water and let it sit and brew), then let that cool, you can put that on the nipples with a compress and let them sit in it a while. It has a lot of tannins and helps toughen up the skin.
I hope you do OK with this and can keep nursing. If you need to, there is NOTHING wrong with supplementing again. I know where you're coming from, my son was bottle fed and breast fed his whole time, which started with his having jaundice just like your baby.
I definitely agree that you should seek a lactation consultant or if there is not one in your area look for a LaLacheLeague leader. As a last resort you could try an attachment parenting or moms group etc as there are often knowledgeable women for support but you always risk not getting "correct" information as it's mostly "this is what worked for me" and might not help you or may send you in the wrong direction. But if it's your only option it's worth a shot. Also how long has it been since you switched back? With both of my boys I had that 2 week "conditioning" period where it felt like razor blades every time they latched on then all of a sudden it goes away and everything moves into a routine.
Also at times my nipples looked the same as you are describing after finishing nursing, but the pain wasn't there. I don't know that what you are seeing is that terribly abnormal, but the pain isn't something you should have to have all the time. If he's 3 months you may also be starting back to full time nursing at the same time he's hitting a growth spurt and nursing more vigorously to up your supply. Good luck and please seek help from someone trained in this. And remember no matter what you are trying your best and are in NO WAY a failure!