Yes, the original siding should be removed.

Yes you need to remove the siding but why are you considering replacing it ?

Sorry, I have no vinyl siding now just the original cedar wood boards. Wanted siding to avoid painting. Was told the original boards need to come off. I don't know why that bothers me. New to this reno stuff, thought you could just vinyl over the boards. I suppose I could but read this could cause problems, like bulging, due to weather temps. I live in the northeast so I feel our weather does not go thru extremes throughout the year.

Most likely I won't be getting to this part of the reno until next spring or summer so I have time to decide and if I go vinyl or similar product, guess I will have to remove the boards. Right now I'm leaning towards paint, spend the savings on a boat and let whomever inherits the place deal with it. Lol

That sounds like a fine plan ;)

I would say you can hang vinyl siding right over the top of the cedar. Many manufacturers have shapes that will work with what you have underneath and there is great vinyl these days. And cedar siding....keep it, one way or the other, on preferably. Go into a real lumber yard and find out how much yours costs now, go home and re-evaluate the value of your siding and home. Renovate it if you can and replace some, treat, oil stain, or oil prime and paint over... or vinyl side over with a grade of vinyl that makes sense. But, you can see how expensive a mistake it would be to get rid of the cedar for nothing. Cedar is usually knotless or #1 grade, few mills, and it would cost you so much to replace it all with new cedar. Keep researching, for a guy you would like to do your job.

Please reconsider the use of vinyl siding. It's a petroleum product meaning that if your house catches on fire, it will burn hotter causing much more damage to your home. The smoke from the vinyl siding is also much more toxic so if you should be near it, it's going to be much worse for you than 'regular' smoke that is already extremely toxic. My husband told me this when our neighbor decided to burn a stump out of his front yard that was 6 feet from his vinyl sided house, and my husband and I were discussing the insanity of it. He's been a firefighter for 30 years, and this is what he's seen and been taught. Sorry if it offends anyone.

I agree with refurbishing what is already in place. While I suppose vinyl siding has gotten better over the years, I just feel it ages more quickly. Cleaning your walls and applying a new finish to existing material is usually the best and most cost effective way to go. I sided houses for a little over five years and think it would be a shame to cover up good materials, and existing craftsmanship of your home.