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The advantage is actually not that great. If you play a lot you do get more retainers and more experience for your general but it's overall strategy and tactics that will win you the game. My general currently has 8 stars and I remember when I started off I beat a 7 star general without using any veteran units or retainers.

As to how the players are matched, if you let the game manage it, it will try to find a player of your level if one is available, if not, it will keep searching for any available player of sufficiently close rank.

• You can place up to 10 ships in 1 fleet
• You can put 1 fleet into a trading port
• For each trading ship (war ships have no effect here) in a fleet occupying a trading port, you get a certain amount of money each turn.
• The amount you get is calculated every turn, so if you remove a trading ship from that fleet, you will earn less money next turn from that trading port
• If you put at least 1 trading ship on an trading port, a trading route will appear between that trading port and one of your coastal cities.
• IIRC, you can check the amount of money from a trading route simply by hovering your mouse over it.
• You can see last turn's total trading route revenue in the balance sheet.

The best strategy to maximize revenue from an trading port is to put a fleet of 10 trading ships there and park some escorting warships directly next to it. The zone of control from the warships do not prevent enemies from attacking your trade fleet, but they will join the battle.