It does get better, but you may need to work on your latch. You shouldn't keep having a lot of chapping and bleeding once the latch is good and the nipple has healed. If you have a lactation consultant available have them watch you nurse and give suggestions, and also check for tongue tie.
I just kept reading articles on good latching and trying to make adjustments until it gradually got better. What worked for me:
Holding the breast for baby
Side lying nursing
Cross football hold, and bringing baby straight in
Switching sides every two hours - helped me with oversupply but might not be good for everyone
Good luck, Mama, you are doing great!