Is it possible to reassociate an annotation centerline?

If reattach isn't working, then you are in the same boat as all of us.

Although, I will point out something:

You can create centerlines on geometry 2 ways (there are probably more...)

way 1)

The way you have been doing it, by selecting the two edges, and then dragging the end of the centerline to finish.

way 2)

If the hole was created in one feature (hole wizard hole) then just selecting any face of the hole will add a centerline to the entire length.

Here is an example:

In this example, the 2 counterbored holes to the left and right were created in one feature, so just selecting any face of the ID of the hole neatly dropped in a centerline.

The middle hole was created in 2 features.

There, I have a choice.  I can do what you see here, and then drag the end of the centerline upward to complete it, OR I can select the face of the large counterbore and it will just add another centerline.

I think that selecting the face is also a little more robust because when you are moving the section view, you lose the hole edges created by the section, but you don't lose faces of the holes.