Antique dresser- restore or update?
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Because this is an family antique, I'd try to restore it.
For the chips, I'd use a wood filler and stain. Or you can go to a wood store and by thin sheets (veneer) of real wood that could be glued over the filler. If it is not too extensive, maybe putting a little money into it and taking it to a wood refinisher would be the best.
For the stain on the top, depending upon where it is, I'd leave it and put a dish to hold jewelry or something on top. Sometimes, trying to refinish just a section will make it look worse. You may end up having to refinish the whole top to blend in.