Please keep in mind that as I write this post hubby has worked 4 shifts currently totaling 44 out of 66 hours. Add 45 minutes getting geared up per shift, (+3hrs) and you have 19 hours left to sleep, eat, and spend time with the family. His work week ends Saturday afternoon, he is scheduled for 15 more hours.
I have already raided the chocolate stash.
#5 won't go to bed without his roommate, #4.
#4 won't go to bed if he knows he is missing out on ANYTHING (including teeth brushing or peeing) that #1-3 are doing.
#4  share a bedroom wall.
#1#2 share a room and like to chat at night.
#3 sleeps upstairs in a cozy little quiet den. Best room in the house, but he needs to be tucked in.
#1-4 won't go to sleep until they have all kissed the babies/toddlers (not sure what to label them) at least 12 times, and snuggled them, and read stories with them, and they usually try to squeeze in some jumping on the bed.
Translation: All 5 kids have the same bedtime, its awesome.
So I get to brush at least 2 sets of teeth per night, and I try to 'check' the others at least twice a week, while #5 is crying at my feet, Exhausted, but refusing to go to sleep because #4 still needs his excema cream smeared all over him after I have pinned him down and brushed his teeth.
I nurse #5 while #4 runs around the room yelling about his cream stinging.
I switch sides and continue nursing #5 while #4 builds a nest to sleep in.
Both little boys are nodding off when their siblings come in to kiss them goodnight and chaos ensues.
I nurse #5 again to calm him down and #4 rebuilds his nest.
#5 goes to bed, I kiss #4 who now needs a story.
If I tell #4 a story, #5 will want to come snuggle and if I say no #4 will scream until #5 joins him and then no one sleeps.
#4 will not stay in bed until #5 has had at least 2 minutes of snuggling (thats what he says, "brother snuggle me for 2 minutes?") yep, too cute to resist.
I tell #4 a story, and #5 comes to snuggle. Then I rock #5 while #4 asks for a bedtime song.
I get #4 & #5 in bed.
I tell #1&2 to climb in bed.
I run upstairs and tuck in #3.
I run downstairs to find #4 is upset because he can't find his blanket/pillow/stuffed animal.
We find the right item and put him in bed.
I tuck the girls in bed.
#4 runs to go pee, leaving door open and lights on.
#5 wakes up.
#4 crawls in bed, tosses the 7th blanket (he has to have at least 3) out because it belongs to #5.
#5 snuggles up and nurses, again.
#4 dozes off.
#5 goes to bed.
#1 or #2 sneak out to inform me they are scared/worried/forgot some homework.
Usually takes at least an hour to get them all in bed.
Sometimes I might hear them sound congested and sometimes I might tell them there is a bottle of Benadryl* in the cabinet, cause I am off duty.
*my kids really do have allergies and while I joke about using it as a sleep aid I use it as directed, the sleep aid effect is just a bonus.