I consider my children to like sleep although they woke overnight for feeds frequently (especially DD1), they were both very easy to get to sleep and resettle. They never fought over sleep so it was not really a challenge or problem for us and we didn't want to make it one. They both had fairly long naps with resettling (say 2-3hr naps with one resettle during). My four year old still doesn't fight sleep when told it is time for bed, she never tries to come out of her room or stall with endless requests. Sleep in our house has always been pretty great, thankfully.

It isn't something I talk about unless it specifically comes up or I'm asked. I generally try to phrase it in a way to reassure people that multiple wakings isn't necessarily a negative and keeping sleep 'positive' has had long term benefits for us to maybe inspire others who are currently in the deep end that there is purpose to their investment rather than a straight out bragfest. Basically trying to emphasize that it wasn't the amount of sleep that made things easier but the attitude surrounding it and sometimes it can help others to redirect their focus also. I'm sure there are times it has made people annoyed and that's okay too, sometimes people need places to focus their frustrations.

I don't think you should feel uncomfortable talking about your child and circumstances, it is your truth. People can hold the capacity to commiserate and celebrate in equal fashion, it need not be one or the other. If people do respond badly then just remember not to take it personally and it is more about where they are in their journey than anything to do with you and yours. But because on the other side it is very difficult to be sleep deprived, sometimes it doesn't hurt to be mindful of that when choosing your audience. Although everyone should be able to share their stories (good and bad) without the other person automatically making it about them (and their own situation), sometimes people just aren't in a good place to separate things like that so it does take awareness from both sides to acknowledge that and act accordingly.

It isn't unique to sleeping either, there are lot of things people feel they need to hold back on publicly celebrating for fear of offending others (breastfeeding achievements, milestones etc) but I think it is something that should be less taboo when handled with care. When in doubt, just be completely honest "I really don't want to feel like I have to keep positivity about my child's sleep to myself but I feel guilty because of where you are at with yours and I really feel for you and your situation so I'm not sure what the best way to go about this is..."