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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. 

Minimal maintenance is required, though regular inspections to ensure insulation hasn't shifted or deteriorated can improve performance over time.

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.

Ductwork should be wrapped in insulation in certain locations. This includes unconditioned interior parts of the home, such as attics, crawl spaces, basement ceilings, and between floors. Duct joints should also be insulated since they're more likely to leak air than other parts of your system. Building codes in some areas also require ductwork to be insulated.