P.,
congratulations on sticking through it. breastfeeding is one of womens' great tasks in life. tenderness is not uncommon. i'm wondering why are you having it now, after 2 months. did something change in the way the baby is feeding? you also mentioned not having enough milk.
what i think about with all those concerns is how well the latch is. i know, that's something that is concerning in the first couple of weeks. but with adequate milk supply, the baby can gain weight even with a poor latch.
i suggest getting in touch with a professional ASAP to assess your latch. you want to make sure the baby has a deep asymetrical latch. that ways it will be more comfortable for you and more efficient for baby.
for now, express some breastmilk and rub on the nipples and areola (the dark part) then let airdry. if you are having problems with dryness, you can try 100% lanolin (there are a few brands on the market) that is made to soothe breastfeeding moms.