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Another vote for Port Royal & Patrician (I like the third one). Don't forget to check out Imperialism II too!
Take a look at Europa 1400: the guild. It doesn't fit neatly into any of your requirements, but I personally like it's business aspect. It also has some political intrigue built in for added value.
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Brian1014: However, I'm mostly looking for games at the moment to help kick my MMO habit. Something to occupy a few hours in the evening between making and eating dinner and putting the kids to bed...something I can pause when one of them starts screaming and my wife gives me the look that says "Your turn"
Understandable. I have very fond memories of New Horizons. It was cool to find the Moai Heads and to get that special ship from Nippon - all the while circumventing the globe. Here's hoping that Koei would find success in the Western PC market with Nobunaga's Ambition and decide to bring a Uncharted Waters V westside. :)
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.
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Matewis: Hardwar. This is definitely one of the best games I've ever played. It's been many years since I've played it, but I recall that it had quite the interesting trading/economy model, ranging from the purchase of properties, to you chasing after bandits, or chasing after police chasing after bandits, so that you can salvage the scrap of the bandit's ultimate wreckage and look for a place that will give you a good price for it.
I can echo that. It's basically Elite, but set on Saturn's moon (Titan). There are factions to contend with, and you can be a bounty hunter, scavenger or trader, or whatever mix of those professions you like best. Traders are better off because that usually doesn't require much fighting, unless you want to deal in riskier (and highly profitable) wares like narcotics. After a while you can purchase your own real estate and set up shop there for extra income. AI pilots follow a dynamic economy, with variable prices for goods, as well as some resources becoming scarce or abundant There's also a pretty good story driving the singleplayer campaign.
Somebody should have mentioned this already: http://www.gog.com/game/x3_reunion
The X series from Egosoft WAS mentioned already but I agree, it needs to be on this list.

Hmm, all the games I thought of have already been mentioned by others. Good list, keep them coming!
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Sachys: Somebody should have mentioned this already: http://www.gog.com/game/x3_reunion
I did get the X games...or several of them anyway, based on the recommendation. I can't comment on it though personally, because I just couldn't enjoy the movement of the two I tried. Maybe a combination of inexperience with flight sim type games and no controller input. Maybe the steep learning curve most reviewers mention. Probably that I just suck.
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Sachys: Somebody should have mentioned this already: http://www.gog.com/game/x3_reunion
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Brian1014: I did get the X games...or several of them anyway, based on the recommendation. I can't comment on it though personally, because I just couldn't enjoy the movement of the two I tried. Maybe a combination of inexperience with flight sim type games and no controller input. Maybe the steep learning curve most reviewers mention. Probably that I just suck.
I think x3 actually had partial controller support... maybe it was x3: terran conflict.

They're a bit odd to start with control-wise, but it does get a lot easier after and hour or so.

As to learning curve, theres a really good beginners guide on the egosoft forums - tells you a few basic "buy this, go there" runs to start with and explains things like setting up automated trade (with the trading software mk3 you can buy for your ships).

Personally, i suggest using the custom start and selecting a pirate for getting used to combat - you get a fairly good ship and will be seeing a lot of fighting. Play that for an hour or so and you'll be good to start proper.
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XYCat: How about Sid Meier's Pirates?
i 2nd this.

(... atmosphere, exploration, crew and ship upgrades)

Have all that and the side quests are pretty nifty too.
Taipan!