Sorry I don't have time for a long reply. Ultimately you have time for your baby to latch but milk does need to be removed from the breast regularly by baby or pump at least 8 times a day to achieve a full supply.
It sounds as though feeding at the breast is important to you, so expressing (in particular hands on expressing) can be revisited as a plan B.
In the meantime here are a few ideas to read around about how to make breastfeeding potentially more comfy.
Starting with nipple shields as mentioned upthread. It's always worth considering trying to achieve a deep latch even if nipple shields take the pain away. This can be done by following the information in the Global Health Media video Attaching Your Baby at the Breast, or you could think about nipple-to-nose, waiting for wide gape, lips flanged outwards, supported spine but head gree to move.
Here's some info on nipple shields which do carry a risk of infection, especially theush (keep clean and replace regularly to minimise this) as well as reduced supply in some mums.
abm.me.uk/breastfeeding-information/using-a-nipple-shield-with-a-breastfed-baby/
The flipple is a technique to shape the breast
themilkmeg.com/get-better-latch-exaggerated-latch-flipple-breastfeeding-technique/ especially koala hold
Laid back breastfeeding / biological nurturing can help your baby get a deeper latch
www.royalwolverhampton.nhs.uk/services/service-directory-a-z/infant-feeding/laid-back-breastfeeding/
Consider high arched palette which can go hand in hand with tongue tie - case study here
abm.me.uk/wp-content/uploads/2018/03/mag8-featured.pdf
Skin to skin can also keep the breast a nice place to be, help with hormone regulation and give you chance to enjoy your baby.
I'm wondering if you have a local support group you're in touch with? Many are running via Zoom. La Leche League or the Breastfeeding Network might have local groups or you might find one on Facebook. You could also ring one of the national helplines.