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Yes, wainscoting is installed directly over drywall. However, ensure the drywall is in good shape since it will support the wainscoting. If the drywall has issues, such as holes, mold, or mildew, repair them before installing the wainscoting. Alternatively, you can install a plywood substrate before attaching the trim.

You should always hang drywall from the top down. Starting at the top makes it easier to create a straight, tight line between the ceiling and the wall. Any gaps that occur will be at the bottom, where they are easier to manage. You can either cut the bottom piece of drywall to fit the remaining space or cover the gap with baseboard trim. Additionally, starting at the top is physically easier, as you won't have to fit the top sheet into a tight space between the lower sheet and the ceiling, or try to balance the upper sheets on the lower ones while securing them.

Yes, you can install drywall over plaster, but there are important factors to consider. While it can create a smooth, flat surface, it is often not the best approach. Installing drywall over plaster will increase the wall's thickness, which can cause issues with existing window and door frames that may no longer fit. You might also need to adjust power outlets to keep them accessible. A better, though more expensive, option is to remove the old plaster and lath entirely before installing new drywall. Drywalling directly over plaster seals in the old material, and if any problems arise later, you will need to remove both layers down to the structural beams for repairs. Given the potential complications, this job is best handled by professionals.

If the holes in the plaster are small, you can fill them with layers of patching plaster until they’re filled. After it dries, you can sand the plaster and paint over it. If the hole is much larger, consider using bonding plaster first and then a layer of patching plaster, completing the process with sanding and a layer of paint.