Weatherstripping .

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I am in the process of replacing the weather stripping on my garage door. Have removed the old weatherstripping. Haven't put the new one yet. Upon closing my door I find a gap (very small opening) towards one side. While most of the door closes fine (Again, the door is without weather stripping now) is this small gap at the very end something to be looked at by a professional.

Also do you recommend priming and paiting the base of the door prior to installing the weatherstripping. As such there are very minor dents and wood imperfections caused due to pulling the roofing nails needed to remove the weather stripping. Or just use a wood filler to fill the small holes and go ahead and install the weather stripping.

Thanks.