You would if your truck rots out because of it.
If the tops never been off, they can easily leak when you pull it. GM didn't use anything on the seals when they were installed, they sometimes adhere to the cab, then when you pull it, they rip. The glue bonding the seals to the topper can pull loose when you pull the top off. The seals harden with age and exposure to the elements. The small amount of butyl rubber GM used to keep the water out of the truck right where the bedrails meet the cab also typically gets destroyed when a top is pulled, if that isn't put back, water can and will leak in under the topper right there, and sneak in behind the fabric/cardboard sides of the bed right at the B pillar. At which point the water hits the seams that are behind the cover, and proceeds to rust. The metal isn't painted as well behind those as it is elsewhere that is visible, so rust on the surfaces is more likely as well. Water there also rusts the screws and metal mounts that hold on those side panels, which makes them a pain to remove in good shape. If the cab starts to fill up water, you'll be lucky and know you have a problem, if it's a smaller leak, by the time you notice, there will be holes in the metal. If the water leaks in the back, you may end up with holes in your bed.
Ask how I know all this.
If you pull the top, be prepared to replace the seals if it's never been off, and whether you have to replace them, (or not, if lucky) use silicone grease on the seals before you put the top back on.