Emma, I don't co-sleep (would love to but my boys for whatever reason prefer their own sleeping space) so I will leave part 1 to someone else. As for part 2, Tom is similar to what you describe. He usually goes down for his first sleep sometime between 8am and 9:30am, although if we have playgroup or something he often doesn't have a first sleep. Then what happens depends on when he woke from his first sleep (could be anytime from 9 to 11:30).

To my mind, routine and predicatibility is about order rather than structure. So roughly speaking, Tom's day is wake, breakfast, maybe bf (depends on the day), sleep, bf, lunch, play, bf, sleep, bf, play, bath, bf, dinner, bf, bed. But the order can change and he can miss a sleep or have an extra one. But more or less the order of things is the same. And also when it varies significantly (ie miss the first sleep), it's because we are out, so he then knows that means that he will bf and sleep as soon as we get home. So he still knows what to expect IYKWIM?

So I guess what I'm trying to say is that if you follow your baby's cues, things will pretty much become a routine anyway, just a more flexible one. I hope this makes some sense for you. I find this more so with a second child, as the two of them have to fit into each other's patterns to a certain extent, and most often that means all my shopping is done late afternoon as it's the only time neither of them needs a sleep.