The trading company does not cost too much. You already have the ships, so why not make even more money. The key to the ideas is greed. If you just wanted to commit a few crimes and live well, you'd be independant. Guilds are about making scads of money. They are driven by greed. As such, you have to make every gold piece make you at least two more. That is why trading companies. You aren't gonna send a whole boat for a few crates, so you make more money by hauling legit cargo. Same as modern cargo ships carry a whole bunch of different commodities. A big ship is cheaper to run than a horde of little ones, so jam the thing full.
The other reason you don't want to sell items in the same town, or to an unscrupulous merchant is two fold. One, if I'm a guild leader, I'm going to be a bit paranoid. As such, the person moving my stuff is gonna be someone I have dirt on, or a family to hold in ransom. Therefore, I'm not using just some merchant, I'm using one I have in my pocket, besides, middle-manning doesn't make me as much money as going straight to the source (again with the greed).
Reason two, an item in the same town garners attention. With the nobles hob-nobbing together, one is gonna notice when their whatever is in a friend's trophy case. Bad for me, as it increases my chances of being caught (side note: Guild leaders ALWAYS keep a number of patsies lying around, especially those that don't belong to the guild or know what the heck is going on, that or just charm them). Also, magical means can outline a lot on an item. Therefore do not steal highly rare or special items. Too hard to move (only a few people want them) and they tend to be noticed. Go for the quick sells.
Okay, now, here's a few dirty tricks for making those items disappear without a fence. If an item is non-magical and is a precious metal, it is often worth it to just melt it down. You lose money, but it's safer to pawn off a lump of silver than a candle-abra. Or, if you have your hands on a few coin minters, just make the local coin and you can spread your loot that way.
Now then, here is one straight out of history. It's called shaving. What you do is this. We'll say the country you're in is using precious metal (gold, silver, etc) for coins. What you do is take a sharp tool and shave the edge of the coin. This peels off small parts of the metal, which can be melted down and minted into more coins. Becareful, do this too often and you notice the coin getting smaller and you can feel it weighs less. Coins value was based on weight and purity. The problem with this is that it tends to only work on a large scale, otherwise you take too long to make it worth it. For DMs wishing to make it harder, pick an appropriate skill and make a check. I suggest Craft, with its own sub-group for shaving. Give synergy bonus for people who work with precious metals or work at jobs where exactness matters (like shaving a person's face).
That's it for this one. PLEASE don't ask how I know this stuff.
