I will start with this: everyone should get your hands on Gloomhaven. It is a work of art, and an example of brilliant game design. It is a game which is more than a bunch of wonderful mechanics put together coherently. It is an experience, one that is greater than the sum of its parts.
Most of what makes GH interesting is the sense of cohesion throughout the game. There are many chances at drawing random event cards and resolving them, but while these are arguably random, the events somehow feel related to one another and relevant to the player characters. Many decisions throughout the game have long lasting consequences, be it adding or removing items from the deck, or leading you to another mission, there is a feeling that your decisions as a group has a real impact on the overarching story of the city of Gloomhaven.
Speaking of which, I am sure that many have already read enough about the game to know that characters can retire, and they do so once their life quest is up. This has led to some concern from some players, and honestly I too did not want to let go of my character as I had grown so used to it, but the way I see the game is that we are all telling a sweeping tale of the city of Gloomhaven. That is, the main character of this story is the city itself, and not our characters. This gives a very interesting feel to the whole game, where you are sometimes made to look at the game, the city and its environs from a much larger perspective.
While the game can be fiddly in some aspects, the game is really not that all complicated in terms of the rules. Perhaps it does have many moving parts, but I found a wonderful resource in the form of Gloomy Companion. This web application handles most of the tracking of hitpoints, statuses, as well as the enemy cards and attack deck draws. I am not sure if this is an officially sanctioned app by the creator, but it reduced the setup time and admin time so much that I can’t imagine playing the game without it at the table anymore. My only comment is that the AI is incredibly detailed, and might require multiple checks against the FAQ and forums to figure out. Interestingly, I have even seen training pages dedicated to interpreting the rules properly. That being said misunderstanding some of the rules doesn’t dampen the fun of the game at all. I am just not one of those people who need to get it all right all the time to have fun, and trust me, the game is hard enough already.
If you are interested to play a character in a city who wants to feel like your decisions really matter, pick this game up. Run out and get it. It is worth every cent you can get it for, and you will appreciate its genius once you actually play it. This is an experience you would not forget for a long time.