Mostly looking for PC or maybe DS... would listen to PS3/2 if you have something amazing in mind.
This is what I have and what I think of them to give some idea:
Patrician4 is okay but it's really repetitive and the satisfaction wanes.
Freelancer-esque games feel too much like the trade aspect was tacked on rather than being the main focus/income.
The Guild II:Pirates of the European Seas is near perfect in what it does well, a little wonky on some things, but just plain too reliable to crash and corrupt your save to be playable.
Recettear had some great shop aspects but the dungeons got tiresome for me.
Chocolatier (on Steam) is fun for a bit, but too casual.
Tropico is fun but off target.
I'm considering a Harvest Moon - I have the PSN one and it scratched a similar itch.
Can anyone suss out what I'm looking for and point me in the right direction?
Thanks in advance PA
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I don't know of any modern game which meets requirements either, but let me give you two off target recommendations: Pharaoh and Settlers 2 (though the last one is really a traffic management sim if you take a step back and look at it).
Otherwise... I don't know... there was something called... Monopoly Tycoon? A very weird real-time version of Monopoly... of sorts... anyone remember it?
I know that 2 is really good, not sure about 3!
I like making people happy.
Since you mentioned the Guild, you might like the Anno series. The one just prior to anno 2070 (1604 or something) would be my recommendation. It should be fairly cheap these days.
Another I just thought of is that Omerta game that's coming out later this month. It's an organised crime business sim by the people who did Tropico 3 and 4.
I could also suggest X3: Terran Conflict (you can get it on Steam). Which at first glance may seem more of a space combat type of thing, but I assure you the trader/business manager side of things is where the real fun is. Setting up a complex inter-stellar trading empire has never been so rewarding as it is in X3. Though, admittedly, the game is fairly complex and will probably take awhile to get used to. Plus there are a plethora of mods to make everything all the more awesome (in fact some mods take things a step further and allow the player to set up their own Space Empire).