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.
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.