I’m a tabletop gamer Dad and I feel your pain here.
In the words of our Master Cecil concerning Dungeons and Dragons:
“It has one billion rules. It involves constant mathematical finagling that would constipate Einstein.”
Im kind of looking forward to the new dnd digital table top software theyre coming out with. I think it might help me bridge the gap between video game and role playing game.
I hear its a long ways out though. The current beta of the simpler one on dnd beyond.
There are several third-party ones which are already available (and have been for years). Roll20 is one of the big ones, and it has a lot of support already built in for 5E, including packages for most, if not all, of the adventure books which WotC has published.
WotC has been working on their own VTT platform for years, dating back to the 4E era. It remains to be seen if they can ever actually get it out the door.
I played originally with the Basic boxed set in the 70s in grade school, our DM had lost his dice and was 9 years old with no allowance for new ones, so we were playing with a spinner board salvaged from some Parker Bros game with the dice numbers written around it in crayon. My first level thief died from a kobold arrow in my very first session.
So began a multi-decade hobby, though I don’t play anymore due to time and kids, but look forward to introducing my kids to it in a couple years when they are old enough.
In high school we played RPGs during lunch for a while but due to stupid rules about “gambling” we weren’t allowed to do anything involving dice or cards. It doesn’t matter that the game had nothing to do with gambling, if dice or cards were involved in any way it was forbidden. So instead we had slips of paper with numbers on them and would draw one from a hat instead of rolling a die. It sucked but it worked.
The irony is that we wanted to gamble, that could have been a way to do it.
The first game I played was with the original Basic Set with chits you could cut out from the back cover instead of dice:
My first character was a Thief named Darren. All these years later I can still remember how exciting it was.
I’ve heard that the game is popular in prisons, too. And prisoners also often have rules against dice, and so similar workarounds are used there, too.
I heard this as well, first-hand unfortunately.
Prison, high school, potato, potatoh. 
I had the original Basic Set. Just like the one pictured with two major differences:
1 - It came with dice. Very cheap dice, low impact dice that quickly became rounded.
2 - The module was B1 - into the Unknown. It was a simple dungeon crawl, but eash room was blank. They expected the new Dungeon Master to add the monsters themselves.
I guess I’m lucky - I have an 11 yo daughter and am DMing for her, her older sister and my wife.
Both girls also play in games with their own friends (the younger one is currently DMing).
They are now collectors items. 
Yes, super lucky! My wife refuses to play with us 
So I went down a rabbit hole of VTT’s and I ended up setting up a campaign on foundry VTT over at the forge. Having fun creating it so far, I’m just hoping my son will be willing to give it a shot.
My wife doesn’t play in a lot of games with me, but she’s been doing it intermittently since we left Uni in the 90s.
Outstanding - I’m glad to hear it!
About five years ago, I introduced my girlfriend to D&D.
Last weekend, my wife started her second concurrent campaign as GM.
And they say you can’t win at D&D.
The original 1980 column is a rather hilarious read, one of the classics that pulled me into the Straight Dope universe early on:
Do they both play in the same party?