Last night at 10 minutes til 9 , , , and makes what H calls 'the deal'.
Hey Heather sorry to hear about this problem in your life. IMHO, the bedtime routine is too complex, too many steps.
Granted I'd the dad of teenagers, but I am able to remember what bedtime was like way back when, and out routine started @ 8 with bath time, then brushing teeth, 3 books (or later 1 chapter of a book) and then potty. Lights out at 9. It was an hour to wind down as someone else noted.
My input: It's important for you and H to discuss this at a time other than bedtime, away from D5. Explain your concern about S5 getting enough sleep and being alert in school to H. Ask how much sleep he thinks that S5 needs (nicely).
Also, you didn't mention what time S5 wakes up. Is he getting 8 hours of sleep?