What's everyone think of Guild 2? I bought it when it first came out (and the Pirates expansion for it), but I never really gave it a chance. And now, here I am back with the first game.
Neither of them were particularly well-rated, but I at least find the first game absurdly captivating, almost sickeningly so (I have to control my play time, or I just sit and play and play and play, obsessed). Guild 2 in particular seems rather underrated (if not just in the US).

The Guild actually got pretty good reviews. Generally 7.5 - 8. 5 range. Guild 2 wasn't that well received, though. Supposed to have a lot of technical issues. Generally most people seem to prefer the first a lot.

The Guild 1 is MUCH better gameplay wise. Trust me, I tried out The Guild 2 and it was too slow paced for me whereas in Guild 1 you can set your own pace as far as the acquisition of money is concerned. The Guild 2 actually makes your character WALK to a twon hall or wherever you wish to be whereas Guild one you just point, click and you are there instantly.
Believe me when I say The Guild 1 is well worth your $9.99. :D

The Guild 2 is not good. I have it.
It's hard to understand, mostly due to the pretty bad translation work (yes, it's worse than the original) and that it's mostly all learned through chasing people and talking to them (at least, that's what I found). That's not helped by the clunky controls.
Stick with the original, it's better than sex.

It's amusing to play to see what parts of it are "broken" - there's a lot of problems with people standing inside building walls, people getting stuck walking in circles, cutscenes where they shout at themselves and others for no particular reason, or all of these at the same time.
As a game, that you paid for... don't. There's a lot of problems, especially with the computer-run businesses. For example, if your starting business makes food, there's a good chance you simply won't be able to make anything because the AI doesn't know how to use farms very well; often, they will just let one or two types of goods take up all their storage space, and stay like that for the rest of the game.

Guild 2 experience:
"Okay, so it's more like the Sims... go over there please. Now... start a relationship with her, who is supposedly most compatible with me."
*click* * click* *click*
"Why isn't he moving?"
Five more minutes of this.
"Alright, finally he's there... in the infirmary/barbershop thing for some reason... "*click* *click* *click*... "argh! Talk to her, move dumbass......" *he randomly goes and does as he should, after fifteen minutes of trying to get him to.*
"AHA! Excellent, and... what the... why's she lying on the ground? I have to choose another potential bride to pursue? She's DEAD?!"" *stares at the screen.
"Fine then, go start wooing this girl, she's the next most compatible." *click* *click* *click*... "*sigh* MOVE dummy"
Five minutes later...
*click*... *click*...
*exit game, uninstall.
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Guild 1 is great... not perfect, but great.