T.S.
I have learned with my own children that responsibility means learning self-accountability. If we are constantly reminding them then we are holding them accountable instead. Most of the things that we are constantly reminding our children about have natural consequences. If they don't, then we can simply create appropriate consequences and then let go of our attachment to whether the child has to deal with those consequences. Too often as parents we are robbing our children of responsibility and consequences.
In Parent Effectiveness Training, they teach a concept about 'who owns the problem'. Too often we take on something that really isn't ours to take on. We have to be careful as parents to be curious as to whether the issue actually has consequences for us or they are really just about the child. For instance, with small children, if a child isn't getting dressed on time who owns the problem. Well, if the parent is attached to the child being dressed a particular way then that could cause the parent to be late for work. However, if the parent lets go of this and simply takes the child to school in their pjs then the child has all the consequence and will learn very quickly what they need to do.
I think we don't, as parents, give our children enough credit for their innate ability to solve problems and understand how to change behaviors to change the effects in their lives. Our children are usually highly creative and intelligent and more than capable of solving whatever shows up for them. Even with the teeth thing, I know that my children have become much better at caring for their teeth after they each had a cavity filled. Natural consequence.
Something else to keep in mind is that clearly reminding over and over isn't working. Insanity is doing the same thing over and over expecting a different result. Instead create consequences, some of those consequences will be rewards like allowance or praise and some will be 'negative' such as having things taken away or not being able to go do things they want to do.