This house was built in the 80’s; cedar siding and peeling everywhere. Not really sure what’s on it in the previous coats, but now has a solid stain. Not sure just yet if its oil or latex. I definitely need to power wash it and scrape it. Do I need to caulk every bored? Is it best to use an oil primer and what kind is best for cedar? The home owners said the previous owners always had a problem with peeling, I’m guessing they never let the cedar dry before painting. Is it better to reuse stain or can I use paint? I’m sure your busy but am hesitating to start this large job. Thank you.
Do not caulk each board to each other- the overlap. But do caulk the but joints and against any trim, windows and doors. You can paint but if a lot of the original "paint" comes off you can use a solid colored stain. Stain has advantages but only if it is applied to raw unpainted wood, over paint a solid stain is no better than the underlying paint.
If you decide to paint definitely use a standard oil base wood primer. This will soak into the wood. Even better is thin the primer a bit (so it soaks into the wood) and apply 2 coats then paint.
Go ahead and wash then scrape and see what comes off then proceed accordingly.