I'm not sure where you're located, but I would try to find a lactation consultant near you who can do an in person consultation. They can discuss latch issues, pumping issues, etc. Your health insurance should cover a consultation, if not I would Google if there are any lactation consultant programs near you, the students should also offer free consultations!
Ask your health visitor if they can offer any support with baby’s latch, or if they have a breastfeeding champion on their team that can help you. There are also private lactation consultants that you can see. I saw a private lactation consultant and a woman through the HV team, honestly the HV woman was so much better and more helpful. She was a breastfeeding specialist. She supported my breastfeeding from about 6 weeks to 12 weeks and was honestly amazing. Also you can ask for a tongue tie referral if you think that’s why he prefers bottles. Even if he was checked at birth, it’s worth checking when they are a bit older. With the pump, try massaging your breasts while you pump and also double/triple check your flange size. It should only be 1-2mm bigger than your nip, most women end up using one that’s too big x