My house came with plastic faux shutters which were attached with plastic shutter anchors. The idea is that you drill a 1/4" and shove the anchor in and your job is done. Unfortunately, with a little wind the anchors pull out or they snap off, leaving your shutters barely clinging to the side of the house or flying down the street in a storm.
Over the years I've tried several approaches to reinstalling the shutters, many of which required getting the remnants of the previous plastic anchor out of the hole. It is tough to get leverage to drill into the wall while perched atop a 25 foot ladder and can be dangerous if you push too hard and tip the ladder over. The fastening methods I've tried previously didn't last, were too expensive or were too permanent. (If the shutter itself breaks, you need to be able to get the anchors out!) I've finally found a method that meets all my criteria and is easy to perform at high altitudes.
Step 1: Supplies
What I eventually found is pocket hole screws. These are self-tapping screws with sharp points and intended to bite into wood and pull themselves in. They have thin shafts and wide thread pitch in order to keep wood from splitting and this accommodates a wide range of play between the existing hole and remainder of the previous plastic anchor. You can even improvise and use a sliver of wood or old shutter anchor as a shim, in the event you find a hole where the previous anchor has pulled all the way out. Pocket hole screws have square heads so you can get torque to drive them in without pushing so hard that you almost tip the ladder off the wall. Finally, the pocket hole screws are long because of the nature of pocket holes so it is easy to find them in lengths to fit any thickness of shutter and have enough left over for the anchor holes. Because the pocket screw heads are small, I also used some fender washers.
1) Pocket hole screws
2) Fender washers
3) Spray paint to match the shutters (not pictured)