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Hello there, fellow GOGers.

Couple of years ago I was checking some old reviews and stumbled upon Europa 1400, also known as The Guild. What intrigued me was that this game is so unique I couldn't even compare it to anything I knew. The idea of playing everyday life of a thief or a gravedigger(!) in Middle Ages really sparked my interest.

Now we have here The Guild 2 and other games with similar title that befuddle me.
So here are some questions for someone who played the games or simply know the answers from some source:

1. What are all this different Guild 2 games? How are they connected? Are they all stand-alone expansions of original Guild 2?

2. I like starting the series from the beginning, but sometimes you can safely skip previous games because the later iteration has everything the original had and it's much better (for example I don't need to try Anno 1602 or Anno 1503 after playing Anno 1701 first). Is this the case here? Can I skip the first Guild with clean conscience and start with some of the other games from the series?

3. This is not a question but if you'd like to add anything or share some info you think I should know before diving into series, please do so.
This question / problem has been solved by mushroom_ffimage
I'll try to help out a bit.

1. The first game "The Guild 2" has a campaign to play through, and a sandbox mode, which IMO is the bread and butter of the game. I forgot if "Pirates" has a campaign or not, but it adds new jobs and things to the game. Then lastly, "Renaissance" I don't think has one, but adds even more new jobs and other fun things into the mix.

2. #1 kinda answers this. As you get to the newer games, they add new stuff and are really just kinda like expansions with a few changes, so it's basically just an upgrade of it with each new game. I personal never touched the campaigns and had oodles of fun with the games.

3. The biggest thing to have in mind when beginning this series is that there will be bugs. There will be many bugs. Sufficient to say, make sure you install the latest community patches. If you can put up with the bugs, you can really have allot of fun with this game.

Maybe someone can give some better input. :)
Thank you, mushroom_ff, for your answers.
I was looking for more detailed ones, as I'm still in the blur about these titles after your reply.
Both me and questions are still waiting. :)
I waited enough and as no one tried to get more into details, I've marked mushroom_ff's post as the solution.

(Finally) Done some of my own research and it turns out The Guild 2:Renaissance have everything as previous The Guild 2 games plus some more features so I'll start either with original The Guild or The Guild 2:Renaissance.
The rest can be ignored completely.