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you can carry multiples of everything if you want, but weapon and armor bonuses don’t stack. A great sword and dragon slayer don’t give +2 to non dragons. Chartering ship allows you to leave a location (like the ruins) to travel elsewhere (dark tower).  Maybe you want to earn a little gold at an easier location before delving into the darker places, or you weren’t feeling a location that day but didn’t want to forfeit the gold and equipment you’ve earned so far.

One more nit pick. Can you sell equipment back to the shop when upgrading? 

not by default. The shops doesn’t want used equipment. It’s value plummets the moment you wear it off the lot