Is there a reason why olympic skateboarders receive more leeway to land their maneuvers than olympic gymnasts who need to land their maneuvers the first time?
I'm not sure if there's a good answer for this one that is not almost completely opinion based (unless some standards body has published their criteria for creating the current scoring system).
The scoring drives how conservative or risky you can be while still remaining competitive. That reflects one way that the standards-settings bodies for these sports differ.
Compared to organized gymnastics, skateboarding has a tradition of emphasizing new, varied, and risky maneuvers. I think using gymnastics-style scoring would create an environment where the top performers would feel pressure to perform only solid tricks. By having a large number of discards, the athletes instead should be able to select tricks that are closer to the edge of their ability without fearing that a miss will doom their competition.
Opinion time again here. I think that a gymnastics meet where the top few athletes all performed what is the the current "top move" in some discipline and the spectators got to see how each executed it could be a fabulous event.
I think a street skateboard competition where the top few athletes all performed the same trick would been seen as a problem.
It may be an unsatisfying answer, but the real reason is that Olympic competition for a particular sport is run by the rules of that sport's international governing body, not by any one body (i.e. the IOC). So, for example, FINA, the world swimming organization, may have different false start rules from World Athletics, which runs track and field. So swimmers would have different false start expectations than runners.
(I'm just using false starts as an example here; I know WA has changed false start rules in the past, and I don't actually know how they currently compare with FINA's rules.)