What matters IS what is in the person's heart when saying it.
God understands where we are on our journey. As the toddler wants his favorite toy, or needs her favorite blanky to feel secure and consoled, we parents understand they need them. I think God understands that those who rely on repeating those prayers over and over, like to say them, for it makes them feel secure and consoled. It's not sinful or bad per se, just does not carry the same weight as prayer from the heart. It is worth saying from time to time as it is instructive to us as to how we should pray, i.e. what our attitude should be.
I just read the hail Mary prayer, the first two times I read it, I was appalled, but I assumed I was missing something, so I read it again with a more analytical attitude, and I think I understand it now. Here it is:
Hail, holy Queen, mother of mercy, our life, our sweetness and our hope. To thee do we cry, poor banished children of Eve. To thee do we send up our sighs, mourning and weeping in this valley of tears. Turn then, most gracious advocate, thine eyes of mercy toward us, and after this our exile, show unto us the blessed fruit of thy womb, Jesus. O clement, O loving, O sweet Virgin Mary! Pray for us, O holy Mother of God, that we may be made worthy of the promises of Christ. Amen.
It is a little confusing, at first I read it as the prayer is saying Mary is "our life, our sweetness and our hope", but I assume it was a continuance of listing what she was the mother of. At least I hope that is the meaning of this prayer. It could have been worded better. Still find it wrong to call her "most gracious advocate", and to say she has the "eyes of mercy".