It depends. If you get a door that is a different thickness than the one you have now, then you have to replace the entire jamb (and trim) which is a lot of labour. If you replace it with a nearly identical door (same thickness and dimensions), then you may be able to do it yourself without any hassle. I replaced a plain Masonite steel door with a masonite door with a full height glass insert, and it was no big deal to do myself. My house is fairly new, so this was easy to pull off, though.
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