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Yes, insulating ductwork in a crawl space is a worthwhile investment, especially if you live in a colder climate or run your air conditioning for most of the year. Uninsulated ducts can lose up to 30% of their heating and cooling efficiency, which can significantly impact your electricity bill. The project is a relatively small investment and typically only takes a few hours. It's a particularly simple add-on if you are already hiring someone to insulate the entire crawl space. An added benefit is that insulated ducts put off less hot or cold air, making them less attractive to pests.

If you’re using faced insulation with paper, face the paper toward the inside of the room during the installation process. 

A good way to remember this is that the paper should face the “warm side” as it’s the vapor barrier, meaning it should face toward where the heat will be coming from.

When installing board and batten siding, make sure there is wall sheathing and a moisture-resistant barrier installed. Behind that sheathing should be plywood or OSB for you to nail the boards and battens into. If there isn’t plywood or OSB, you can install vertical furring strips at 1½- to 2-foot intervals to nail the boards and battens to.

You do not always need to remove old insulation before adding new. If the existing insulation is in good condition—not wet, physically damaged, moldy, or infested with pests—you can add new insulation directly on top of it for a compounding effect. You can also mix different types, such as adding blown-in insulation around existing fiberglass batts.

However, removal is recommended if the old insulation is compromised by water damage or pests. You should also remove it if you plan to install a different type of insulation, like switching from roll or batt insulation to spray foam. If the existing insulation is very old or damaged, you will likely get more benefit from removing it and starting fresh.