We have 5 Johnson pocket doors in our home and put small, clear silicone bumpers at the very top and bottom of the door. Three of them were installed 10 years ago and still work fabulously. I love them and love the extra space in bathrooms in particular. The bumpers not only protect the wood, but also make them much more quiet.

The above process works well for a painted jamb, but not a stained jamb. The generally requires replacing the damaged portion---the one side as you put it. The snag in replacing the one side is in how the top portion was fastened to the sides and the threshhold. The side piece is set in a dado(groove) and fastened with staples, while the bottom is usually screwed to the threshhold from the underside of the threshhold. It is not too difficult to cut the damaged piece in half and gently work the side piece back and forth and pull it apart---but the staples remain---which makes installing the new piece properly impossible---as well as the screws in the threshhold. So, the best way to replace the side jamb is to remove the entire door assembly, unscrew the screws, pull the staples, install the new piece---after making the mortises for the hinges---and reinstall the assembly. Adding the metal backing and using metal screws to install the closer will help prevent a re-occurrence.

Not sure what facilities and equipment that you have. The newer urethane glues (Gorrilla and others) make it possible to glue in another piece and then machine it to match. I recently had to do an jamb extension on a split-jamb door to fit a wall that was too thick- explanation about that is far too long. Had to remove the casings from that side and disassemble the jamb assembly. I glued and used 18 gauge brads for the extension strips, then a portable belt sander to bring them flush. Reassembled the jamb, reinstalled the door assembly. Invisible after painting.

Everyone has different tastes and styles. My personal preference when it comes to wood or log homes is cohesiveness and distinction of what is accent and what is the main feature. For example in your first picture, it would be nice to have a solid wood or knotty wood door walls all over the house where only the doors and windows (with their respective trims) are solid white or vice versa. Mixing them is challenging because the materials are different and wood carries more visual weight so when your eye sees it, there is competition happening. In the first pic for example, I would actually paint out the knotty pine trim around the window and door so that they look seamless and your eye flows over them or put in a window and door that are knotty pine and keep the knotty pine casing/trim. This way you have a clear distinction between the "feature" and the "accent" whichever way you go. For your louvered doors, if you want them to disappear, paint them out in white along with the trim. If not, re-stain them along with the rest of the wood doors and baseboard trim. My two cents worth! Best of luck!