According to Craftsman National Estimator, "High time difficulty factors for surface preparation and painting. Painting takes longer when heights exceed 8' above the floor. Productivity is lower when an application requires a roller pole or wand on a spray gun or when work is done from a ladder or scaffold. When painting above 8', apply the following factors:

Choose the best quality paint you can afford; it lasts longer. Experts estimate that the outside of a house should be painted every 5-7 years, but less-expensive paint may start peeling or fading in 4 years or less while really high-quality paint will hold up a bit longer. Better Homes & Gardens[1] describes and compares the different types of exterior paint while[2] reviews specific brands.
Painting exterior windows depend on the size of the window and the number of panes. To calculate the price for windows larger than 15 sq. ft., add 1’ to each side of the window and then multiply width x length. Add two sq. ft. for each window pane for painting the mullions, muntins, and sash and then multiply your total sq. ft. by $84/100 sq. ft. So a 4’ x 4’ window with 4 panes will come to a total of 44 sq. ft. x $84/100 sq. ft. = $37.
Following the same process as the primer, cut in the walls with your chosen paint. For best results, paint one wall at a time. This makes it easier to spread the paint while it’s still wet. Work from top to bottom, rolling the paint in V or W-shaped strokes. Before applying a second coat, wait two to four hours. Then proceed with the same process used for the first coat.

Expect to pay between $600 to $3,500 or $1.25 to $3 per square foot to coat vinyl, with prices likely increasing for the finish. It is one of the more inexpensive siding materials to have repainted, especially with recent innovations in materials. Changing the finish on your siding is not recommended unless it's completely degraded and worn away by the weather. You can save nearly half the vinyl siding installation cost of $4 per square foot by painting rather than replacing. Before adding a new coat to vinyl siding,