"It works with the latest expansion Renaissance" you say? But that's a standalone expansion not even available on GOG! You sure I can install that on my "The Guild 2 Pirates of Whatever"?
Sorry for the lack of answer I didn't get an email there was forum activity. The guild 2 is weird as all its expansions are stand alone but seem to work with each other to see the other expansions/original game content (otherwise the latest expansion contains parts of all the previous expansions which would make no sense). I should have looked but I thought gog had all expansions but its missing Venice and Renaissance but they might add them in future. I'm not sure how well the gog version will mix with using expansions from different sources like steam. The legacy mod pack works only with Renaissance version, its gets installed into the renaissance directory, it should work with steam and non steam versions. I use the steam version original with Pirates and Renaissance together (plus the modpack) you no longer use steam to run the game with the modpack but use the exe file of the game directly.
To Nirth, I haven't played much other than to test out if each profession has the ability to make equalish amounts of income and test out the new things added. I didn't play any serious game as the version I had used was buggy and crashed a lot, I was waiting till it gets updated and more stable to play seriously but seems to stay now at version 1.0991 and that version is much more stable. The difficulty really does effect how aggressive the AI is, on hard they insult you and send thugs quite often but on easy they seem to leave you alone. It also takes some time to get used to resource changes as now some buildings require some other resources and also produce some different items.