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I auto trip my fleets but take manual control when they get near my home port. I use my initial cutter to hold a Salesmen captain. I produce a second single ship fleet and captain with a Haggler. Both of these I keep in main port. I try to make all my other captains for fleets for trading to have captains with either the Navigator skil for 20% faster sailing or Organizer for 20% more load. When I get a fleet in I change the captains so I have the salesman to sell, then the haggler to buy goods for the trip. then I replace the original captain and set him to autosail to his destination. This way I get the best buys and sells in my home port. 5% bonus both ways increases profit tremendously for really a small amount of upkeep.

If I use organizer I transfer 20% of the load before I change captains to the warehouse so there is no lost cargo. Then change to salesman, sell, load up the rest of the goods in warehouse and sell...then switch captains to the haggler...buy 20% of the load and put in ware house then full load. Switch captain back to organizer and transfer the rest of the 20% back into ship. All Sales always done by salesman in home port...All buys always done by haggler this way.
 
Yup, that's a really good idea. To exploit even more you can store in your Warehouse for a while allowing for prices to climb up... or sell to AI who in general pay more than your home market.

The difference in skills comes from difficulty level I think, on Hard you don't need Navigators and Organizers that much, you rather need Salesmen and Hagglers since you have to care about selling and buying prices more than about getting more quantity of goods to your ports. Often Salesman+Haggler will be the only way to profit from this goods at all, because without either skill you won't be making profits. Then you can add Organizer+Navigator... but it will only reduce your profit margins faster so the additional income from them will quickly diminish.

So yeah, for Easy/Normal it's better to go quantity but not going quality on Hard means a lifetime of poverty.
 
My port strategy is this

1. Build a upto a lvl 4 Trading post in one of each MBT. All others I keep at lvl 1. Destroy bigger ones as necessary.

2. Ports I have 1 level 1 in each general area. Destroy all others. I will if I can afford to build those up to LVL 4 if I am doing well and want to start upgrading fleets after 1630 with a better ship design since build times for these larger ships is quite long. Sometimes 1 lvl 2 or lvl 3 port in india is nice to quickly make a defensive fleet or a fleet to attack some pirates or something like that quickly. A small fleet to shift around Iron Wares is also nice in the India area.

3. Warehouse - keep at Lvl 1...unless there becomes a good use for them in an update....its just a waster of money to upgrade above lvl 1. A lvl 1 warehouse can supply enough materials for atleast 2 upgrades. Destroyable but 500 pounds is not much.

4. Forts and garrisons....Garrisons seem to me to be the way to go atleast for the first 50 years....a level 3 garrison of 750 men can normally be a good match for a fleet of loaded of Galleons. I normally will leave a lvl 1 fort standing if one exists. But either way....a garrison level of 3 is highly desirable if you want to keep the port. I don't believe the AI attacks your ports until a certain date, Atleast 1615 I believe.

So lets look at this. A port for resupply would be 1500 for the trading post, 500 for the warehouse (optional), no port or fort. and 10000 for garrison lvl 3 so 12000, is the reduced amount atleast for the first 50 years. I also only take resupply ports for 2 reasons, first is to garrentee I dont have fleets going out of supply and secondly to force my enemies to go out of supply. Like 1 example is to take Jadida, The Canaries and Cape Verde, with these 3 most of your enemies will go out of supply while heading back to their homeport and vise-a-versa. This slowdown can be very nice to have. In an easy or normal game you should be able to support a few ports fairly quickly, but each port does take profit. If you dont want to support a port, why not destroy all buildings then release it? By destroying all building you can be garrenteed an easy invasion if someone you dont want takes it and it will take him resources to upgrade, second, when you do take it back over you can destroy the buildings again and release it again.

I do take the initial port in the Indies when given the chance, its well worth it, it normally has the all building at level 1 and upkeep is not that high at lvl 1 buildings. You could drop the port and and fort if you like right away. Other buildings would be unwise to destroy in my eyes.

Well I hope this helps.

Also you can see how I am usinf dual fleet convoys in my AAR
 
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I Build 2 xubecs and begin a life of piracy.
I take whatever i need off pirates or any other nation that does me wrong.
Commanderring ships is by far the cheapest way to build fleets.
The only ship i buy after my 2 xubecs are eastindamen when they become avilible
 
I just started
I see that spices are giving a lot of money back
but I couldn't go through 1650 as I lost most of my fleats in wars again spain and netherlands... (I was playing Portugal)
Now I will restart a new game... probably with portugal again

At first I made a fast fleat so that I can do missions in one year

one war fleat,
a few merchant fleets
 
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