I think it depends how old your LO is. At a year old, I imagine it would be more difficult than 2 years old and that would be more difficult than 3 years old and so on.
After my LO's second birthday, I night weaned her gently (Dr Jay Gordon's method) so that cut out a couple of feeds. I don't think you need to think about drying up milk - by that age, your boobs will probably be quite responsive and able to cope with changes. LO is 2.5 now and usually has a morning and a bedtime feed but she can go without one if she's distracted or we're really busy. It'll be a slow process from here and I imagine there will be times when she feeds more, then back to less again, but a general trend of less as time goes by.
I'm sure that if you follow LO's lead, even if you initiate the start of the process, you don't need to worry about pain or anything - weaning is a gradual thing not a sudden stop.