When we are ready to go to bed, we take our dd to bed with us (if she isn't already asleep). So if we were going to bed at 8 pm, so would she. In general, this has worked out really well since the beginning. If the whole tribe is hunkering down, turning out the lights, and well nursie-ing :-), dd figures it must be time to go to sleep now. Occasionally, there have been times when dd could not get to sleep when we were going. Then one of us stayed up with her awhile, quietly, trying to encourage sleepiness (e.g. dh would take her for a walk). It wasn't much of a routine, either timed or with habitual parts: it was just time for the family to go to bed.
Re: bonding with my dh, small children generally sleep longer than adults at night. (That's certainly not an absolute, but most do, and we were lucky enough to get one who does. :-)) So in general, dd will either have conked out a couple of hours before dh and I are ready for bed, or she will sleep a couple of hours after we wake up. Another thing she sometimes does is take an evening nap in preparation for staying up until the family bedtime (which isn't at a regular time, but there's a ballpark). We value our alone time while dd is sleeping, or hanging out with her godmother in another apartment. But it isn't our only "dp-type" bonding time, by any stretch. Sometimes dd is busy by herself in another room. When she was a baby, she might be hanging out in the sling, and she didn't seem like a fully separate person yet.
If my dd were going to school, it would be by her choice. One of the things we'd discuss ahead of time about school is how you have to commit to showing up at a certain time, every day. We'd talk about how we'd all (since dh or I would have to take her) need to start going to bed earlier, to get to school on time. I'd probably try to get her directly involved with the alarm clock, showing her how to set it and letting it ring until it woke her so she could turn it off. If I had needed to take dd to a babysitter or daycare earlier on, I probably would not have woken her. If she'd woken up because of being moved, that reality would simply have incorporated itself into her natural sleep pattern. (This did in fact happen when we had to go somewhere and dd was still asleep.) She might have taken an extra nap later, or an extra long nap, or fallen asleep earlier that night.
Are you familiar with The Continuum Concept? It sounds to me sort of like you're asking if letting sleep happen when it happens is necessarily child-centered (used pejoratively -- i.e. child-centered in an unbalanced way). To me, it is just the opposite. I go ahead with my adult activities, my adult sleep habits, etc. When she was a baby, I carried Grace in a sling or in arms a lot while I did this. Whenever she was ready (not necessarily in two regular daily blocks) she would nurse to sleep, or fall asleep as I moved. Sometimes she seemed restless, and that cued me to lie down and nurse her (which is the first way she learned to nurse, as a newborn). If she seemed really asleep, and I wanted some space, I would put her down. Dh did the same things, except that he gave her to me to nurse a lot. When she seemed overtired or was crying in late afternoon/evening, we assumed this was a problem and found solutions (energy-discharge-oriented ones, mostly, and lighting).
We are going to have a baby in a few months. We'll do the same thing.
So anyway, sorry to have written a book, but what I'm trying to get across is that I think letting sleep happen whenever and wherever fits into a larger lifestyle. If that's not how you do baby care, or if you are naturally a routine-oriented person, it won't be hard to get your baby to slip into a routine, and it's perfectly healthy -- if that's how it works (as opposed to requiring night after night of suffering and crying). Personally, it would have been really hard for me to adjust my life to a rigid sleep routine. I've noticed I'm not the only one in my neighborhood, though most little kids nod off in their strollers. I think it fits well with life in the city, where you have to do a lot of things outside your home and transportation sometimes takes a long time (and doesn't involve a car).