Some will argue that the rudder has more advantages because it will save time and allow the vessel to travel more frequently I'm not going to argue against that
RS Gold, however I've always performed ports in a much more relaxed than efficient manner so I always get rudder first.
Then, the ports themselves: What's the best port to upgrade? I've observed that most upgrades are reasonably expensive. I've been trying to upgrade my office to unlock a 3rd ship, but it's just too slow to collect bamboo.
The ideal is to prioritize upgrading to unlock new ships because of obvious reasons, so you're doing that right. I'm convinced that all upgrades are worth the investment (except when you have more than one upgrade, you can unlock them all , however you only have one active at the same time so choose carefully).
In my crew, I have 4 'bureaucrat' (well the ideal scenario is having the best ones available at any given time, I can't remember the names of other so I chose bureaucrat which is the primary crew member who boosts the stats of other crew members) crew members. And that's followed by 4 Morale and 5 Seafaring and 4 Combat members 4 Special crew members (the ones that unlock by special trips, like the Feral Chimera)
The crew configuration has always been successful for me, but there's most likely better ways to set up. I'll likely get rid of the Merchants shortly and will soon be able to get more specific crew members or something since, honestly, I rarely use Merchants
Buy Old School RuneScape Gold. They were only useful in the process of acquiring trade items to create the armours.
The Wall