Karen,
I know what you mean with all the questions we ask ourselves in regards to our kids' behavior! Boy!
Kept having those all the time before I finally realized that what my kids do is normal for them and so what if it's not according to the "guidelines of Dr. Spock?" ha ha. Not to say that every now and then I ask myself "where is this coming from and is it okay?" Think those questions will continue forever!
Obviously we see the things that do need correction and changing to help our kids, but I just found in the whole scheme of things, so what if my son likes to sleep on the floor by the door? Or yes, it's normal for my daughter to ask me at least 2-3 times the same question to ensure that she can believe what I say and my answer will be the same each time. These little "quirks" for lack of a better word are part of my kids and the hard part was me realizing and accepting that I didn't need to change anything, just continue to reassure and support them. If my son is 15 and still sleeping on the floor, well, I'll cross that bridge when I come to it. And even then I might not worry about it.
Like you say, every parent hopes their children will be able to go out in the world individually and be happy. For us, we might need more creative ways to help them achieve this goal, but that too is part of parenthood;advocating for your child.
Crick