There are perhaps a couple of underlying questions here. More specifically: What is the system for regaining lost lives (hearts)? It seems you can buy them back (which I haven't tried) or collect ...
Some of the map spots in Scurvy Scallywags are timed bonus areas with multiple types of gold - coin piles, gold bars, and (IIRC) money sacks. So that I can maximize my looting, which of the items is ...