Re: Discouraged and depressed.
Welcome, mama! I'm sorry your nursing journey has been so rough so far. I had similar issues to yours and I know how physically and emotionally painful it can be.
The fact that you are seeing lipstick-shaped nipples after a feeding says to me that you have a latch problem. It doesn't matter if your latch looks textbook-perfect on the outside. It's what it feels like on the INSIDE that matters! The difficulty with milk transfer can also indicate a latch problem.
The good news about latch issues is that babies generally outgrow them. A tiny baby has a tiny mouth, and even at the best of times may not be able to take a deep "bite" of breast. The bigger the bite, the deeper and better the latch. So I encourage you to keep going, keep putting him to the breast, keep working on it. I had cracks, pain, and milk transfer issues for about 4.5 months- well, actually I had cracks and pain for that long. The transfer issues sorted themselves out at around 3 months. Anyway, just when I thought I would never heal, and never nurse pain-free, things turned around and I was able to nurse my baby until she was 3.
One thing you mention which is very normal is baby taking a bottle even after a long nursing session. Most babies will do this, because they love to keep sucking and don't mind eating until overfull. What may help is to get a professional scale and do several days' worth of weigh-feed-weigh records. You may be able to identify certain things that you are doing that contribute to more successful feeds- things like nursing position often make a big difference. And you might find that your baby is getting more from the breast than you think, potentially enabling you to ditch the bottles.
Hang in there, mama! I know this is awful, and I can't imagine how hard it must be with and older kid and a pair of special-needs toddlers in the house, but we'll be here for you every step of the way.
Coolest thing my big girl said recently: "How can you tell the world is moving when you are standing on it?"
Coolest thing my little girl sang recently: "I love dat one-two pupples!"