How hard is it to replace siding?
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On a scale of 1 to 10 for someone who is not construction savvy, a 9.
An Introduction to Installing Siding - Better Homes and Gardens
There is mire to it than meets the eye. It can be difficult in that you have to get the measurements right and have to match up corners. For wood siding — pull the old off, which is typically nailed on. Put the new on and paint. Vinyl siding is a bit more difficult. Here is a guide that will give you more of an idea as to what is involved:
https://www.familyhandyman.com/siding/how-to-install-vinyl-siding/amp/