It is very simple and should be done at least annually. There is a cover plate that is commonly held in place with two screws. The plate fits around the chainplates on the deck. Remove the screws and tie/tape the plate up and out of the way (no need to remove the shrouds). Scrape away all of the old sealant and clean the area thoroughly. Lay down plenty of new sealant (DO NOT use 4200 or 5200) and rebed the cover plate.
As far as sealant goes, I recommend 3M 101.
Also, if you have a leak, it may have compromised the core. If that's the case the job will be more difficult. While the cover plate is off, see if the core is wet or rotten. If it is, you'll need to excavate the core around the chainplate, fill with epoxy thickened with colloidal silica, and rebed as described above.
I understand what you're saying. However, the coverplate on the Caliber 40LRC is attached to the chainplate. So, there is no way to lift up the coverplate. On my previous boat, the coverplate could be lifted off of the deck, and the sealant could easily be replaced. Not so on this boat. You can visit this website to see an illustration: Caliber Multi-Bulkhead Bonding System(tm)
click on "Double-Lock Chainplate System" to view. It seems as though I may have to loosen the shroud, remove all the bolts attaching the chainplate to the bulkhead, and then try to remove the chainplate and rebed it in sealant.