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You don't say what part of the country you are located. In any case, the weather can turn from nice to nasty, rain or cold in 1 day. If your going to paint it yourself, it may take more than one day. A professional may take more than one day. So you can chance the weather.
I would wait until spring. The weather can change in the spring also, but the warmer temperatures will allow the paint to set better and faster.
Spring is the best time.
We had our house in California painted in Decemebr. Keep in mind that you may end up with all of your windows covered with paper on Christmas day (we did). Weatehr can delay the painting. It has to be something like 40 degrees for them to paint.
You can always get the prep work done now and paint in the spring. Prep work is what takes all of the time. Painting does not take long at all. Some houses reqruie only a few days of prep work. Our current house needs several months of work before it will be ready to paint. It all depends on how many coats are on it and the condition of the paint, trim and siding.
With good prep work, and top quality materials a brushed job by good painters can easily last much longer than 10 years. A spray job should last 5-10 years depending on your location. In California, we had a spray on job last 7 years before needing repainting. In Mchigan we have relatives with painted houses that were last painted 16 years ago and still look fine. The paint is faded, but still adhereing properly.
The top coat of paint on our house is about 60 years old, but past due for replacement. The bottom coat may be well over 100 years old. I am not sure when it failed.
Usually, the paint on the south side of the house fails first.
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