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Yes, capped chimneys should still be vented. Failing to vent a chimney will result in condensation buildup inside the chimney, which commonly results in mold growth. If mold begins to grow in a chimney, it frequently goes undetected and spreads quickly through the home. Mold and moisture can damage the structural integrity of your home, and exposure to mold can cause discomfort and illness in residents.

In most cases, no, roofers won’t need to come inside. Some reasons roofers may need to come inside are to assess ventilation. inspect roof leaks, or check for any structural concerns.

Most traditional lenders will not loan against a house with a leaking roof, and some lenders won’t lend against a home with a roof near the end of its lifespan. If the roof on your new home is in poor condition, you may need to have the seller offer a credit for a roof replacement after closing, or you can opt for a renovation loan—also called a 203k loan—to bundle the house and the roof replacement into one loan.

While you technically can add a roof over shakes or shingles, it’s not a good idea. Roofing over existing roofing creates a moisture barrier underneath the new roof and since the trapped material is wood, you can expect a moisture problem. While you could get away with installing a new roof over asphalt or steel, wooden roofs should be removed, new underlayment installed, and the new roof installed over that. Also, the extra weight would add strain to your roof structure.