RPG Quests (Family Game Night RPG)

THE GAME: Several times a week my wife and I have a family game night with our kids and we either all play a video game together or some board game. I was working on a Pokemon-ish game for my kids, but ultimately I want something that we can all do together so I got the idea to create a board game -like RPG along the lines of Dokapon Kingdom. Each session will be a randomly generated world with a randomly generated quest (somewhat roguelike in the way that will work), and you will take turns (hotseat multiplyer)exploring and doing all that fun RPG stuff in a race to rack up the most loot, most monster defeats, most quest knowledge (for example, info from NPCs), and ultimately complete the quest. You'll have a persistent character (i.e. carries over game to game) and persistent captured monsters (a small group of which you can bring with you to turn loose on the other players) so that will work in that Pokemon element. As a twist I want to make it so you can play in a heroic or villainous manner (determined through actual choices made in the sessions) so that the players can potentially be playing in direct opposition to each other, rather than just as a rivalry. That would make for some great alliance-making, and possibly some even greater double-crossing.

WHAT I NEED: Each session of the game presents an RPG dilemma of sorts, some catastrophic event that calls for heroes (or villains) to see it through. I need to come up with a nice long list of generic RPG quests that have a set of goals (that can be randomized) for heroes and then a set for villains (intertwining).

Suppose you have a princess who is wanted by the boss villain but held captive by a dragon elsewhere. Playing as a heroic player you try to rescue her and bring her back to her father's castle, playing as the villainous player you abduct her from the dragon and bring her to the boss villain. Defeating the boss villain (who enacts some random evil plot across the land) is the goal of the heroic players, aiding the boss villain in his evil plot is the goal of the villainous players.

Though the players can explore each world (session) at their leisure, certain things only pop up when one of them has acquired the information. So, until they gather info about the missing princess and the dragon from NPCs (etc.) the dragon's cave does not pop up on the map. Getting there (and surviving long enough to gather the info) is where the battling and gearing up takes place, and of course the players will be able to duke it out the whole time (dying brings you to the last inn/etc. visited, classic RPG style). When it comes to heroic or villainous options, the players can shift gears at any time. You could have acted as a villain most of the session, captured the princess to take the boss villain and instead bring her to the king, for example.

I am scouring my frighteningly excessive RPG knowledge, the internet, and replaying some of the classics but any ideas you can provide will be greatly appreciated. I want to make it varied as possible.

SIDE NOTE: I am making this to enjoy with my family the more fun I can make it the better. I will put it out there for free and I will make a devlog which I will try my best to share all my steps along the way for others to learn from or make suggestions for. It will be a free no-strings-attached game, I am making it with Game Maker Studio, It will be for PC though I have a friend with a Mac so I can try to get a handle on how GM Studio exports to it (I have the module, or whatever it is called, for GM). I think making a project that is actually meant for someone (well someones) and meant for a purpose (family game night) and is coming from a wanting to bring people together is the kind of project I have been in desperate need of, and should have been working on all along. It is the kind of project that really sparks my enthusiasm, not just my desire to create. I think this project is good for me, I hope to make it good for everyone in the end.

EDIT: SIDE NOTE 2: I just realized, I have an extra challenge here. I have to create a game that I, myself, will actually enjoy playing (since we are going to be playing it on family game nights).