hi
With regards to breaking the 10.30 habit, I always do the same as you too, wait to see if she settles herself if the crying is hard and distressed. I think that she knows that you will go in and see her if she keeps it up so the only answer would be to not go in if you know in your heart of hearts nothing is wrong, it's just habit.
This is really hard as I found recently with daytime naps. I simply HATE leaving my DD to cry, it tore me apart so much and I would hover by the door but after a few days (5 I think) I found that she would cry between 5 mins and up to 20 mins at the most and then go to sleep. The 20 mins is a well documented common crying duration. If she was still crying after 20 mins I would go to her and get her up and cuddle her as she had really worked herself up by now. lots of people don't feel they can do this and it is hard, but I knew my DD was just shattered and OT and wanted to sleep and the crying was a result of wanting to sleep as I know her different cries.
Keep up the early bedtime if she seems tired late afternoon, it works wonders. I gave my DD an early bedtime last night after she melted down all afternoon and she's still asleep after 7am!
Hope some of this helps in some way. Like I always say, what works for one babe doesn't necessarily work for another. MY DD is an amazing, happy, fun little girl who is so interested in things generally but without her good sleep, like any human, she gets niggly!