If the entire house was updated + you had the addition it could still be questionable. The saying "You never want the nicest or worst house on the street" is very true. By doing an addition and update, are you going to be the "castle" on the street? Are people going to pay 500k for a home on a street with 400k properties or would they go elsewhere?
Then again, if an addition/update will bring your house to be on the same level as others in the area I would say go for it. You always want to get as much out of your place as buyers are willing to pay in the area.
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