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Whether or not the terms of your roofing estimate are negotiable depends on the contractor. Some professional roofers will be willing to budge on labor fees to some extent, while others will simply walk away from the potential work rather than lower their fees. In most cases, it’s best not to negotiate the terms, as lower labor charges could lead to your contractor cutting corners. Material costs aren’t negotiable, but you could purchase them yourself to try to save on delivery fees and markups.

Generally, roof flashing is installed under the shingles to create a watertight seal and prevent moisture from seeping in and causing damage. However, the exact placement can depend on the type of flashing. For instance, with step flashing, the shingles and flashing overlap each other, meaning the flashing is technically both over and under the shingles. Flashing also typically goes beneath the house siding and is often not visible from the ground.

Depending on the type of damage your roof shingles have, you may be able to simply repair them without having to replace them. However, if there are more than a few to repair, replacement is likely the easier option. You may only need to replace a few of them. Repair shingles by applying roofing sealant directly under the shingle's damage and then directly over it. 

A roof replacement can take anywhere from one to 14 days. For most homes, a full replacement that includes tearing off old materials takes about one to two days, though the average project can last up to 12 days. The exact timeline depends on several factors, including the roof's size and complexity, the type of roofing material, the crew size, and weather conditions. Certain materials take longer to install; for example, metal roofs can take seven to 14 days because the material is more difficult to work with than asphalt shingles, wood, or tile. A re-roofing project, where new shingles are installed over old ones, can take half the time or less. It's also important to factor in the time needed to obtain necessary permits. A professional roofing contractor will typically complete the job faster than a DIY approach.