It is not a headache, just that it takes a little bit of time to do it correct, and not mar the wood finish for the trim work. Post pictures. How old is this place? It may be that the roller hardware is needing to be replaced, or needing the bearings lubricated.
As for the resistance, if it is from opening & closing, there is probably something still hanging it up along the roller guide, or the trim is too tight against the door.
As for the resistance, if it is from opening & closing, there is probably something still hanging it up along the roller guide, or the trim is too tight against the door.