Aside from stigma, what are the common challenges or issues that come with extended breastfeeding?

The weaning process is more challenging because your toddler can be very expressive already. They have more teeth too so if they feed going to sleep there is some occasional discomfort for the mom. But since you can reason with them too, you can talk to them about limiting the number of times they feed. My son is 32 mos already and we only feed in the morning when he wakes up and at night before he sleeps. Sometimes for comfort too when he is sick or when he gets hurt