For any others who have had similar cravings, my experiences over the last few months might help.
Mount & Blade was fantastic on a number of levels. Loved being able to trade from one town to the next, doing quests to increase the wealth and standing in different places. The mounted combat was great too, and I usually hate that.
Windward was just as described. The trading was simplistic but fun, not really enough to keep my attention for long. But the rest of the game was...hypnotic. Very soothing, captivating for a week or two. I go back and play for a few hours every now and then.
Of course, either just before or after I posted, Recettear was added, and I sunk a lot of time into that. Not quite trading, but the haggling, the adventuring, the orders and such, it was quite good.
Another addition I came on was Rebel Galaxy. Space trading in Space! Less progress as you do things at stations, but the special events to take advantage of were cool, and the economy was fun to tinker with. Also laser broadsides. Laser. Broadsides.
Cosmonautica was another one I picked up on sale. Lots of fun, trading possibilities were occasionally awesome, occasionally frustrating. I didn't really put enough time into it to overcome those frustrations. The ship management was cool, the crew management less so, the battles rather tedious. But the humor was charming, and the atmosphere interesting.