Usually the font properties are used with Selection.Start and Selection.End properties to select which subset of the string is to be set to bold.
For the two first captions the selection is empty as for the others the selection is the whole text. I don't know how LabVIEW remembers the selected subset of a text so it is better to explicitely set the selection to the full length of the string before setting the font property. You should make a subVI that takes on input the control refnum and that sets the selection of the caption to the full length and then set/reset it to bold. See the attached VI