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We would just go and deal with it. But I've also had pretty laid back babies that can sleep anywhere, usually in the ergo. My older son is almost five and I still haven't left him with a babysitter that hasn't been family or a very close friend!

With very very little ones we brought the pack n play and let them sleep where we were. I knew I could always nurse them back to sleep when we transitioned. When they got older, and sleep was trickier, we've just had to not attend or leave early. It's happened quite a few times.

Yes, this happens with us, usually with my inlaws for the Jewish holidays.
Basically one of two things happens:
1) We skip it (LO and I). Because same as yours, he really doesn't do well with being overtired and its just too much stress for DH & I to deal with it. We live 1.5 hours away and traffic is usually worse with holidays. So DH will go without us.
2) More often, my ILs have just learned to deal with the fact that we need to do things earlier to accommodate LO. Granted their family is small and LO is the only grandchild so its pretty easy to do. But we just said "If you want us to come for dinner with LO, dinner is at 4pm." Its not traditional but its the only option if they want him to attend. And of course they always want him to attend. So we go right after his nap, visit for an hour, have dinner, and usually peace out while everyone else is starting dessert so we can get home by bedtime (which is still strictly 7/7:30 MAX).

I'm insane about his schedule and sleep, so I just don't care what they think. If they want to make it work then great. If they don't, then great. Either way, we're keeping our schedule. They've become pretty good about understanding that.

ETA: Also, his first few months - we just skipped everything. Can't remember how old your LO is, but ours was born early Sept...so height of High Holiday season. We just didn't go to any of the celebrations and the first one was Thanksgiving...and that was a mistake. He was 2.5-ish months and it was too much stimulation and he was a screaming red-faced disaster the whole time. If there is ever another LO, my DH and toddler/big kid will go without me and the baby for at least 6 months.

I have a 6 month old and have yet to leave in the evening. One time my husband and I went to dinner at 430 pm for an hour! That's it. I have tons of family around, too. Its tough. I don't want to mess up her bed time routine. I can't believe I became this person!! As for family celebrations, I have gone and brought baby. I nurse her as usual and end up having her sleep in her car seat. We usually leave shortly after she falls asleep. I keep reminding myself that this is not forever and I actually really still am enjoying my nights in with my baby girl. I just got an invitation to an engagement party and was like "yep, not going!" ugh. I just still can't leave my baby!

I have a 5 month old and I'm strict with his bedtime. I've already used babysitters for various nights out because we don't have family in town and it's important to me that DH and I go out sometimes. But holidays would be a different story because to me the whole point of holidays is spending time with family and following traditions. So, in your precise scenario, I would not want to go to a seder without baby. Can you, DH and DS sleep over at your parents/in laws' house (wherever seder will be)? That way you can see everyone, celebrate the holiday, leave the table briefly to put him to bed and return to dinner. I would also only go one night, not both.

I don't have a lot of family nearby, as I mentioned, but I think a lot of people deal with this problem by offering to host these events themselves (and have others bring food and help clean etc) so the kids can go to bed in the middle and not screw up their schedule.

This is making me realize I don't have Passover plans... guess I should follow my own advice and host a seder!

We flew for Christmas when DS1 was 3 months old and we were militant about his schedule bc my son was/is a hot mess if he's off it. He was doing a 6pm catnap at that age with a 730pm bedtime and a 10pm dreamfeed. We packed our white noise machine and drove our PNP to every relative's house because his waketimes were just over an hour. We said we wouldn't do dinner unless it was at 5pm and left at 6pm.

We basically bathed and had our son in PJs before any dinner time gathering and let him catnap in the car or it a room while nursing at 6pm for 30 mins. Then he could visit until 730pm which by then he was both tired and overstimulated and cranky so no one was bothered when we said he had to go to sleep. We'd put him down in a spare room (or bathroom or closet) in the PNP with his Dohm on and then make sure to be home (or my MILs house where we were staying) by 10pm when we would have his dreamfeed. I might have to rock and hold him more but otherwise his schedule stayed the same.

I would probably opt to do just one of the dinners as opposed to both.

DS2 is a way more laid back baby so it was a lot easier.

Can you just stay over for the night at your parents' or inlaw's house? We are pretty into our kids' set bed times, but we also often travel to see our families and since we are staying overnight we just put the kids to sleep and go on hanging out with our families with a monitor downstairs with us.

When we only had 1 kid we did fly to go see all our old friends in our old state and a few times we put LO1 to sleep at the friends house and then transferred her (by car) back to where we were staying. She was not the type to keep sleeping through transfers, so we did have to deal with her waking up and having to put her back down around 11:30 pm, but it was worth it for us in that case because we so rarely see our old friends anymore (it's not been 2 years since we've been back--now, with 2 kids it's impossible),.

My son is 18 months so older, but it's the same as when he was younger. He has an early bedtime and does not handle being overtired well. I don't take him out to stuff at night unless we are back by bedtime, period. It is not worth it, to us. He's our only so we don't have to worry about another child (yet), but if it was something really important, we would have 1 parent go and 1 parent stay with him.

We had this issue over Christmas at my in-laws, Christmas Eve church started at 7pm central, which is 8pm eastern (his bedtime is 7pm eastern). I grudgingly agreed to take him and it was a DISASTER. 15 minutes in I left early and took him back because he was laying on the floor and screaming.

I think it's up to you to decide what's important. Sleeping over or having family adjust the timing to accommodate sound great. For infrequent things like important family holidays, I've just accepted that the schedule might get screwed up and baby might not get the best sleep that night and brought her with. For me, being with family outweighed one or two nights of non-ideal sleep.

We’ve had great success taking our travel crib and just putting our son to bed wherever we are. Our friends had an Oscar party on Sunday and we all went over ad let him play and eat with everyone until bedtime and then I put him to bed in his travel crib set up in their bedroom. I usually take his white noise and monitor and we can continue with the party. When we have to move him out to the car he sometimes wakes, but usually falls right back asleep once we start driving. We’ve been doing this since he was little, so he’s pretty used to it and does well with it. Some kids wouldn’t do as well, but I think if you start them young, it’s easier for them to be adaptable to situations like this.