Climate guide
Humidity matters more than temperature here, and the shoulder seasons are not the whole answer.
In most of the country the limiting factor is cold. On the Gulf Coast it is moisture, and that changes which months actually work.
Spring and autumn are the easiest windows: lower humidity, moderate surface temperatures, longer usable working days. Winter is genuinely workable here and often underused, since hard freezes are rare and humidity is lower. Summer is entirely possible but the day gets planned around the sun, chasing shade around the house rather than working straight through.
From summer into autumn, storm activity means rain days that nobody controls. That is a scheduling consideration rather than a reason to avoid painting, and it is why we build rain days into the plan instead of coating damp siding to keep to a date.
Interior work is climate-controlled and can be done any month. Winter is often the best time for interiors here precisely because it is the harder season to schedule exterior work. See interior painting and exterior painting.
Yes, with the right planning. The surface has to be dry and there has to be enough time between coats to cure. Humidity changes the schedule rather than ruling the work out.
Not immediately. The surface needs to dry through, and shaded elevations take longer than sun-exposed ones. Coating damp siding traps moisture and the finish fails.
Not if the day is planned around the sun. What causes problems is painting a wall in direct afternoon heat, so we follow the shade around the house instead.
Tell us your timeline and we will tell you honestly what is realistic for the season, then schedule around it.