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

Going for extended breastfeeding can make weaning a bit more difficult. It becomes more of a habit habit when prolonged, making it more difficult for your baby to "detach" from the practice. Here's an interesting article that will help moms decide if extended breastfeeding is right for them. :) https://ph.theasianparent.com/extended-breastfeeding-is-it-for-you-and-your-toddler/

in my case, my baby was more than 2 when i had to make her stop. she used to bite me and i had developed infections all around. so that is an issue, that you can get infections from the baby's teeth. also, it became extremely difficult to get her to wean, as by then she was too attached. i dont think there is any stigma attached to extended breastfeeding.

I think there will be a hard time for husbands and wives to have an alone time since moms are compelled to cosleep with their kid just to continue feeding. But not that it matters, as long as the mom and child desire, extended breastfeeding shouldn't be a problem at all in my opinion :)

Sometimes, kids can be too demanding for the breasts, which isn't really a good thing for a mom who has to finish lots of things at home or for work. And sometimes, the kid just wants to dede out of habit. A bit time consuming, maybe.

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My Son is having severe eczema and diet is really challenging for a breast feeding mum. We are on gluten free, dairy free and eggless diet... but it still doesn't make the skin better. :( 23months old now.

Time-constraint. More often than not, moms who do sustained breastfeeding are glued to their kids and can't pretty much do anything about it unless the kid unlatches.

My wife complains about dehydration and stress while breastfeeding our daughter.