Painting is the home improvement where the difference between a good job and a bad one is almost entirely invisible on the day it finishes. The preparation you cannot see is what determines whether the finish lasts two years or ten.
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The prep section is the part of a painting quote worth reading closely. It should state what will be scraped, sanded, filled, caulked and primed, how many coats will be applied, the product by brand and line, and how surfaces and landscaping will be protected.
On a properly prepared surface with quality paint, exterior work generally lasts somewhere between five and ten years, though the range is wide and driven mostly by exposure and substrate. South and west-facing elevations take far more ultraviolet and weather than sheltered sides and often fail first, which is why you sometimes see a house needing one elevation redone years before the rest. Wood siding demands more frequent attention than fiber cement or vinyl. The largest single determinant, though, is preparation: paint applied over chalking, peeling or damp surfaces can begin failing within a couple of years no matter how good the product was. When comparing quotes, treat a detailed preparation description as more predictive of longevity than the brand of paint on the label.
For exterior work, usually not, provided the crew has access to water and power and you have agreed arrangements for gates, pets and any alarm system. Interior work is different. Rooms need to be cleared or have furniture moved to the center and covered, and you will want to be reachable for decisions about color transitions, trim edges and anything discovered behind furniture. Many homeowners choose to be present on the first morning to walk the scope with the crew lead, then leave them to it. Ventilation is worth discussing in advance if anyone in the household is sensitive to fumes, since low-VOC products reduce but do not eliminate the issue. Agree in writing what will be moved by the crew and what you are expected to clear yourself.
For exterior work, yes in most regions. Painting is highly seasonal, with demand concentrated in the warmer months, so late fall can bring both better pricing and much better availability. The constraint is temperature: most exterior paints have a minimum application temperature and need reasonable drying conditions, so there is a point past which the work simply cannot be done well and a contractor willing to do it anyway is a warning rather than a bargain. Interior painting is far less seasonal since conditions are controlled, though contractors often have more capacity in winter when exterior work has stopped, which can translate into both scheduling flexibility and sharper pricing. If your project is planned rather than urgent, ask contractors directly when their quiet period falls.
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