I'll admit that I know little about how yachting works (aside from my Below Deck exposure), but a consistent theme on these shows that I've certainly also witnessed in other work environments is an obsession with titles. I've always been more of the "screw the labels and just do the work" sort and have observed that often those who are most worried about whether they are "fairly" titled are often undeserving, unqualified or lazy. Perhaps all three. Dylan's obsession with overall experience may be accurate, but Ben explicitly said he chose Sunny because she knew the boat and Dylan didn't. He weighed advantages and disadvantages in making the decision and the captain agreed with him. I think Dylan needs to grow up.