Measure each window horizontally at the top, bottom and middle, from the inside face of the right jamb to the inside face of the left. Record the smallest of these dimensions. Measure vertically from the top of the sill to the bottom of the jamb header at both corners and in the middle. Record the smallest dimension. Make a map of each window's location in the house with a descriptive label of which window it is, and add the dimensions. This is the information you need when ordering your windows.
Familiarize yourself with the various styles of window construction and materials. Consider energy rating, architectural style, the color and finish options available, cost, the quality of construction and available features. Choose windows you like from the premium manufacturers, and make a note of the styles and features you like. Compare lesser brands against these premium windows; some less-expensive windows give you the same options at a significant savings.
Calculate the cost of the project. Include the cost of windows and all installation supplies and hardware. Calculate the cost of labor, even if you intend to do the job yourself. Find out what it would cost to have someone finish it for you, in the event your are unable to complete the project. Price at least three options on your windows to see the price spread for the products you want.
Check with your local city hall about permits and any other requirements. Add the cost of permits, filing and inspection fees, if any, to your budget. Ask about disposal and clean-up regulations as well as any potential fines or additional fees you might incur if the job does not go as planned.
Ask for recommendations from friends you trust if you are looking for an installer. Ask them for the names of contractors who have actually completed similar work for them satisfactorily. Inspect the work, and ask about any issues or concerns they had in working with the contractor.
Contact at least two contractors that come recommended by neighbors or friends or who come highly recommended from their local contractors associations or other trusted agencies or businesses. Ask them about your job; do this even if you plan to do the work yourself if it is your first time. Note the processes they mention, and compare their working procedures to determine what you believe will work well for you.
Schedule the job with adequate time to complete it; try to do it when the weather is not too cold or too hot. If you need to break the job into chunks, schedule at least the first two or three rooms. If you are doing the work yourself, give yourself more than ample time to complete the job.
Get everything in writing when working with a contractor, and read the contract or proposal. Ask about processes or descriptions you don't understand, and be sure to find out what you owe when and what the contractor's obligations are at every step of the project Then read it over again when the contractor is not present to be sure you are not missing anything before signing on the bottom line.
Purchase all materials, tools and supplies, and have them on hand to save trips to the hardware store. Order the windows delivered several days before you plan to install them, and store them in the house so that they can acclimate to the temperature and humidity of your home.