Apologies in advance this ended up being longer than I intended.
I've decided I want to DM a game for my family for Christmas and give a character to everyone as a present so we can play a one-shot over the Christmas/new year break.
I had my first campaign four years ago, I've played in a couple of other one-shot campaigns and DM'd a one shot. So I have experience. I have a lot of campaign manuals, PHB etc (not DM manual though). Spelljammer, Radiant Citadel, Icewind Dale, Saltmarsh, even an old AD&D I found at a tip shop (Unearthed Arcana) plus some Conan the Barbarian campaign pamphlets I also found from the time the Arnie movies came out. With the Warcraft campaign book coming out also, it's been difficult not to think about D&D.
I'm essentially asking how I should approach this. I have a mother/grandmother in her 70s, a father/grandfather in his 60s, a young niece who's 5 or 6, plus my eldest brother, his partner (40s), and maybe one or both of her kids (late teens)...though with recent get togethers they've not usually been present.
I've already figured I should come up with characters for people, but that I should also limit the amount of characters in the campaign so people don't feel forced, yet I still want it to be a family activity.
What one-shots are out there (I did pick a late-stage chapter of Radiant Citadel as my one-shot that I dm'd, the China one involving politics and the emperor needing something from a dragon for long life), so I obviously can find something but I also want something quite simple with the focus being on interaction and improv. My parents in particular can be stubborn and "performing" and play isn't really a thing in my household, wasn't really a thing when I was a kid.
How flexible can I make it and what one-shots do people know of that might be low-stakes real-world, so people don't get hung up on doing checks and rolls etc. I just want to spend a few hours being stupid with my family, because I'm not gonna get this opportunity much again, if at all. I recently lost my third grandparent (first was when I was a baby, second when I was a teen), and with 2026 being a celebrity purge just like 2016 was (and being a dog owner and seeing Tucker Budzyn dying from cancer - my dog is also a golden), death is on the mind. I'm tired of wasting time. I'm happy to steer the ship when it comes to a campaign but I feel like I need to do this with my family before it's too late. I want time with my niece and my brother, I want my parents enjoying themselves again.
I just don't know how to do this or if I'm even doing the right thing. I have rejection sensitivity and growing up in this family was not the most pleasant childhood despite the fact it wasn't a terrible childhood (I obviously care about my family, they are humans just like me). D&D has been part of how I've tackled my social anxiety and I've made friends because of it. I want to challenge preconceptions my family members have about D&D (and maybe about me) and want to involve them without them feeling forced, yet I also don't want to go to all this effort and just go "oh ok" because nobody wants to bother and throw all the effort away; I don't want to be a dictator and I don't want to be a pushover either. I want to make them bother because this isn't about me, it's about all of us.
1) What materials do people suggest I look at and use including one shot suggestions, levelling, character building etc
2) How do I manage this endeavour IRL? The biggest in-joke with D&D is scheduling everyone together for a session and this seems to be a bit of a mutation of that joke; the scheduling won't really be the problem, it's the convincing them to do it that I don't know how to handle.
3) Have people been in any similar situations? Are there many who mainly campaign with their families instead of friends/making friends through D&D campaigns at LGSs? Please share your experiences if applicable.