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Yes, basement insulation needs a vapor barrier due to its susceptibility to moisture seeping in from the outside of the house. You should install a moisture barrier before you install insulation or purchase insulation that comes prebuilt with a moisture barrier to avoid water damage in your insulation and costly mold and water remediation expenses. 

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.

Yes, they address underlying issues, providing long-term seals and energy savings you might need help to achieve.

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.