Which is more fun?

OP is biased - grandfather took 4 y.o. OP to Raccoon Creek State Park where OP promptly stopped a three-person toboggan using a forehead-tree brake.

Only ever had the classic style runner sleds.  Lots of hills, and some clear cut and mowed gas lines.  but no paved roads back then.
So the sled didn’t often work to good.  Never had a real toboggan or plastic/metal disc.
But at some point my dad got a couple rolls/sheets of thick plastic, maybe 1/4”, and maybe 30” wide and 3-4 foot long.  They came from some part of Westinghouse, probably when he was working at the East Pittsburgh plant.   They made excellent toboggan style sleds for the big gas line slope, on the property next door.  But no other kids lived close by, and weren’t big enough for more than one person to sit or lay on, anyways.  But they would fly as I recall.

Depends on the hill and conditions.

Ideal is the multiple person toboggan, but requires a steep long hill and a dense snow cover (or a lot of work to pack down a run).

Runner sleds need ice, but are awesome if they can avoid cutting down to the grass.

The universal good choice is a saucer, or better yet, a snow tube. Light weight, low friction, and spreads the weight nicely - all of this together means works well on almost any hill in almost any condition.