Remember that the nail filler ONLY goes IN the nail hole, not goobed all over outside of it. Put in glazing compound AFTER priming and just rub smooth with your finger. Any work on the outside trim needs to be done with some knowledge of how to keep it water tight. This is called flashing. Calking is no substitute and will always fail eventually. Also, the door frame may be inadequately attached. Many "carpenters" rely mostly on the casing to hold the door frame in place. If your door is like this then it could get all messed up when you remove it and not swing correctly afterward. For the outside, you might want to just apply your decorative mouldings OVER the existing trim and siding etc. This won't be technically correct and pure but if it looks good enough then at least it will still be water tight. If you mess up the exterior flashing then it will leak and possibly ruin your door frames and/or flooring etc. and by the time you notice it could be too late. Pointers: - Pre-cut all your pieces, fit them, then prime and paint them on a saw horse before you install them. Then you will only have to touch up the nail holes and maybe give one last coat in place. It is easier than "cutting in" all those coats of paint up in place. - Attach the trim first only to the door frame with 4 or 6 penny nails and glue and nail the miter joints. THEN, put some nails in the outside through to the framing. This way it is easier to maintain your 1/4" reveal and get your joints tight. - No matter what, always use ear and eye protection when cutting wood! It is easier than ruining your cornea.