heck im willing to pay over 1 million gold just to start with 5 more planks every time i sink or load in. I think they should have 5 tiers of permanent upgrades you can buy just to increase your starting supply by a little bit. i only bought supplies from the shipwright ONCE and i will never buy them again because its pointless to do so. Buying those supplies just like paying to repair your damage or save your cosmetics are just lame attempts at gold sinks in the game. While a lot of people might not think paying a large amount of gold (50 million for example) to boost your starting supply of food, wood, canon balls by say 20 would be that big of a deal it would just be a huge quality of life change for server hoppers to be able to set sail and be stocked enough to at least be able to handle some random pve encounters that seem to frequently hit you when you set sail. heck i ran into some kegs a while back and it was 9 planks to fix all the damage. The maiden voyage sloop for some reason is stocked much better than our starting ships, doesn't make sense. We start with pretty much the same amount of food we always have but the food is half as effective as it was since the introduction to other foods. Not sure why we even start with bananas when it should be coconuts at least since that's what the release build of the game was balanced off.
I would settle for starting with a storage crate but not sure how they would even go about that. However arena ships used to spawn with rowboats so that doesn't seem like it would be too hard a thing to setup.
But you mention the game saving your ship cosmetics so I guess you have lost tens of thousands of gold like the rest of us by playing too much and the game forgetting your saved stuff. I imagine the same issue would happen if they allowed you to spawn with a rowboat the game might just forget you paid a large sum to spawn with a rowboat. If you mean a indestructible rowboat however.... that would be a bit broken. Rowboats with treasure on them use up a lot of server memory so if a player loads up a row boat and leaves it behind for whatever reason it will despawn if no player is nearby. The server basically trying to delete assets that might cause server instability.
Considering they are going 1+ months between bug fixes for captaincy and the last one created even more bugs than it fixed and they don't seem in any rush to fix stuff that's frustrating a lot of the players I don't imagine making improvements to captaincy is even being considered right now as Skull & Bones is right around the corner and going to be trying to steal their players.
