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You can put new siding over clapboards, but it’s not recommended. Some sidings, like vinyl siding, can go over clapboards with sheathing like a foam layer in between. However, it’s best to remove clapboard siding if you plan on replacing it with new siding. Burying wood clapboards underneath new siding can create risks of rot and mold, or hidden insect damage. It can also create warping issues over time. Removing clapboards allows you to properly install a new sheathing, as well as clean up the exterior wall and look for any signs of damage.

How long siding takes to install depends on various factors, but averages seven to 14 days for a 1500 to 2000 square foot home. You may have a longer installation timeline if your house is large or architecturally complex, if you have underlying damage beneath the existing siding, or if the weather delays the installation process.

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. 

You should stain your home's cedar siding every three to seven years for maximum protection and to maintain its appearance. Homeowners who live in harsh climates with high humidity and lots of direct sunlight should plan staining every three years, while those who live in milder locations can plan on seven. In particularly harsh climates, consider using an opaque stain variety for the longest-lasting protection.