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Yes, you can install siding over stucco, but it's crucial to ensure the stucco is in good condition first. Before proceeding, inspect the stucco for any signs of damage, leaks, or mold growth. If you discover water damage, mold, or have ongoing leak issues, it's recommended to remove the stucco completely. This step prevents future problems like mold and pest infestations and allows a professional to repair or replace any damaged sheathing underneath. If the stucco is sound, the installation process involves attaching furring strips to the wall's framing directly through the stucco. The new siding is then installed onto these furring strips. A professional may also need to adjust window and door openings to prevent them from being recessed behind the new siding, which can cause aesthetic issues and create potential leak points.

You should plan to stain or refinish your home's cedar siding every three to seven years to maintain its appearance and provide maximum protection, though some estimates suggest a range of four to six years. The exact frequency depends on several factors, including your local climate, exposure to severe weather like direct sunlight, rain, and wind, the quality of the initial stain application, the type of stain used, and the overall condition and quality of the wood.

For homes in harsh climates with high humidity and significant sun exposure, you should plan on staining as often as every three years, while those in milder locations may only need to do so every seven years. For the longest-lasting protection in particularly harsh climates, consider using an opaque stain.

If you are looking for a lower-maintenance alternative, you might consider vinyl or aluminum siding. While the initial installation cost can be higher, they do not require as much upkeep and can offer more value over time, especially in areas with excessive rainfall or high humidity.

Not wrapping a house before installing siding can lead to moisture intrusion, rot, mold, and even higher energy bills. Older houses may have siding installed without wrap underneath, so it’s a good idea to add a wrap layer when it comes time to replace old siding to prevent potential damage from water intrusion—local codes may even require it, so check with your municipal building authority. 

If you have stucco on the outside of your home, it’s technically considered cladding and not siding, but beyond that, it’s impossible to tell without a little digging. Without damaging the siding material, expose part of it to see if there’s an air gap between the siding and your exterior wall. If there is, you have cladding. If the siding is affixed directly to the exterior wall, you have a simple siding system.