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1

It's an issue of coverage. Using the same color means you don't have to be quite as picky/concerned about even coverage/multiple coats. That said, if you're hiring out, a professional painter should be fine handling a repaint no matter the underlying color.


1

You say it's an old house. I suppose that if the siding was practically at the end of it's rope, plastering it with wood filler might extend its life a few years. I helped replace the siding on an old barn once that was practically plastered with putty. I don't know how long that treatment lasted; I only saw the final/end result (zillions of chunks of putty ...


2

I use a heat gun rather than chemical strippers. It's easier and usually all old paint can be scraped off. Heat guns do have their own set of special considerations and safety precautions but overall it is a better way IMO. That being said, even if you remove all the old paint it is common to be left with a surface far from perfect. I use exterior grade ...



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