When I was a kid, the Team(s) has to get a “Permit” from the City Park(s) for certain days and times. For Games the City would drag the Field and if we were lucky mow the grass. The Coaches usually lined the Field and any other “work” they thought maybe necessary. If there was little bit of rain day or so before Gameday Coaches and some Dads would see what they could to get the Field playable. Not sure insurance had anything to do with this then or now but I do know video games has crushed many kids playing outside!!
I think one of the biggest reasons that kids don't play pick up baseball as much these days than when they did back in my day is that people don't live in walkable towns anymore. If my kid wants to play pick up baseball, he'd have to walk 2+ miles to get to the closest field on a busy, busy road with no sidewalks. When I was a kid, most of my friends all lived close by within a short walk/bike ride on sidewalks to get to the field.
Another factor is that with the proliferation of travel baseball along with soccer and lacrosse, all my son's friends all play different sports. Kids who don't play baseball don't want to play pick up baseball. They want to play pick up whatever sport they primarily play. In my day, everyone played baseball. That is what we did. Then we played pick up football starting around August.
I do agree that video games play a role. I know I wouldn't have played outside nearly as often if I had Madden or MLB The Show instead of Pong.