I've found out the hard way - those that chose a pirates life early on have an up-hill battle with the current rules as they stand.
Thinking piracy would be fun, I spent all my gold on upkeeping and upgrading the Sloop I chose at the start of the game. When I worked out that trading is a safer way to make gold, I gathered the requirements for a Howker and set up a trade route. Foolishly, I lost my Sloop in battle, and all I had invested in it.
In retrospect, losing my Sloop was an act of karma: My Sloop lived by the sword, and died by the sword.
The bit that does sting is that my officers list says I have hired 2 captains, 2 merchants and 2 admirals, even though 1 of each went down with my sloop. For any noob pirate, I can see that being a barrier to advancement. Yes, noob pirates like myself will lose ships (that is just part of the game), but with the current set-up, you could add more and more officers to the hired list, yet only have a small number of ships. This will just end up making it harder and harder for the pirate to build fleets, giving less incentive to play pirate and more to play merchant (or have some players give up the game in frustration when it becomes too difficult to build more fleets)
My suggestion: The costs of hiring officers (for each type of officer) should be based on the number of officers currently hired (alive and well), not the number of officers that have been hired overall (including the dead ones)
PRO: From my point of view, this could be one of those changes that addresses to pirate/merchant imbalance that has been in recent discussions, and would give the game a gentler learning curve for noobs.
POSSIBLE CON?: More experienced players may have more to gain initially, as higher experience means more likely to have a larger difference between total officers hired overall (current rule) and officers currently hired (proposed rule change). On the other hand, this big step-change will more likely be of higher benefit to players that have previously worked as pirates than those who have stuck to merchant routes, so this could be seen as a kind of back-payment for what those pirates should have been given earlier.
I do recognise that this sort of a rule change is one that can make a bit of a change to the dynamics of the game, but I believe it would be for the better (but also recognise that I might be wrong). What do you think?