Actually, I didn't even take the tavern missions for money, either. No avenging anyone, no escorting. Just a few travellers, and the occasional treasure hunt. I sank only the spawned pirate crayers, since my ships mostly could outrun them. I left the spawned cogs and holks alone. Too easy, if captured.
Not many widows anywhere in my game.
The Hanse is doing pretty well, too. Wool is short, so I got wine, which I wanted for the first city in any event. Luebek cannot meet the need. Timber and fish round out the list.
Thinking about a real challenge, I would probably go along with an earlier suggestion here, and use a map of sixteen cities, scattered all over the map. That would allow for 10 new cities to be built. No offices except for the new cities and your starting office. Set trading and the Prince, pirates to hardest of all, and build your hometown to a maximum population. Allow auctions of ships; no captures at all.
That would take some good gaming, real skill. Not for the newbies. Biggest population of your office towns, by a set date, wins.
This current game, you can sell iron goods for 500. Not much difficulty in generating money. That is why I took additional handicaps, to make it more interesting. And did the Danzig move.