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Yes, caulking windows is worth it. Because moisture and air leaks are big sources of common window problems, caulking can be an inexpensive and easy way to eliminate both water and air from getting in. 

It is generally recommended to remove window screens for the winter, especially in climates with heavy snow, freezing rain, or frigid temperatures. Removing them helps prevent damage to the screen mesh and frames that can be caused by ice and moisture buildup between the screen and the window. Taking out the screens also allows more natural light and warmth into your home during shorter winter days and makes it easier to clean your windows thoroughly. In warmer climates where harsh weather is not a concern, the decision is more about personal preference; some homeowners prefer the clearer view, while others leave them in for convenience.

Expect excavation below grade, creating a well for access, weatherproofing, and thorough inspections during setup.

Picture windows last about 20 to 50 years, depending on the material, your location, and how well you maintain the windows over the years. Materials like vinyl and aluminum may not last as long, while fiberglass can last many years. Wood will last decades if you keep up with maintenance. Homes in areas with harsh weather throughout the year may cause windows to have shorter lifespans.