To answer your general question, did I ever wonder if I missed the boat, specifically should I have scheduled my baby's sleep? With my dd, definitely yes, I wondered. I never once was I able to put her in the crib while she was awake, like the books describe, and just walk away. Either I nursed her to sleep, or she fell asleep on dh's or my lap late at night when we were exhausted, or dh walked her to sleep. From the time she was 2 y.o. she could not (would not) go to sleep without dh or me sitting on her bed, reading to her, singing or just waiting in the dark, while she chattered endlessly. It was maddening. It wasn't till she was...4 y.o.? that we could put her to bed and walk away. Of course she'd get up a dozen times before she went to sleep.
Edited to say, really this means that my evenings were almost entirely focused on my oldest for 4 or 5 years straight. But really, I was doing the best I could.