It's all been trial and error for us, trying to find what works, but we are absolutely "schedule" people.  We have twin daughters who were 26-weekers, so after 3 1/2 months of the NICU, we brought them home and went straight to a schedule.  Most people with multiples (unless they are insane or have the patience of Job) will tell you they are schedulers as well.  Our girls slept in their beds starting a week after we brought them home.  We did the "rocking them to sleep" thing when they were younger, but at about 9 months they started wanting to go to bed without it.  So that's what we did.  They started sleeping completely through the night at about 12 months and we've never looked back.  Now, we're transitioning to "big girl beds" aka toddler beds.  Once again, it's all trial and error, figuring out what works best for them.  We did a couple of days where I stayed in there with them until they fell asleep, but I know I can't do that forever.  So, we tried what worked for us when they started going to sleep by themselves in their cribs.  We let them cry it out.  I know some parents think it's horrible, and it does break my heart, but it works best for them.  We let them cry for about five minutes, then go in, put them back in their beds, reassure them, and start the cycle all over again.  The first night took about 20 minutes, the second 5.  Last night, they went to sleep without a peep.  I'm not saying that's the best method for everyone.  But, it's definitely all about trying different things and following your gut.  I read TONS of books when I was pregnant, then after our girls were born. Finally, I threw them all out because they were stressing me out.  I think a lot of moms grossly underestimate what they know innately.  Reading those books, I kept thinking, "I'm not doing that!  I'm not doing that!  Oh, no.  I'm destroying my children."  The fact is, there is always something you could be doing that you aren't.  I'm perfectly happy, though, going with my gut.  It's gotten our girls to the age of two and they're amazing. 

I just go with the flow, and both my kids developed their own patterns/schedules and we've kind of come up with rituals naturally.  I tried Babywise when my first was born and it absolutely did not work for us and now I am totally against that whole idea of that, for us anyway.  I am a very intuitive person and can usually figure out what my kids want right away, and then fix the problem, so my kids are happy.  We are also a co-sleeping family which helps a lot.

Sounds like my daughter has a similar sleep pattern as your son! No night is ever the same twice in a row.

I've always followed my daughter's cues about when to put her to bed...she certainly lets me know when she's tired! These days, she's ready to sleep by 8pm every night, so that's when she goes down.