Hmm, the first few of suggestions I feel answer if you roll threats/despair. If the check is outright failed, I would say they don't enter hyperspace. Proper calculations were not made and system fail-safes prevent entry. With that in mind, I don't always require an astrogation check unless there is imminent drama ("We'll lose them when we make the jump to hyperspace!") or they're attempting to navigate an extremely difficult route.
The key here is that the failure actually mean something. If it's just a routine check and the player simply has an opportunity to keep trying until he succeeds, then there is no point in making the check in the first place. Even with all the time in the world, perhaps failing a check for a difficult route means the player can't try again until he finds some key information he's missing in his data to feed the navicomputer.
Of course, if the plot hinges on the players getting to where they need to go, just "scene wipe" and get there cinematically. Leave astrogation out of it.
I think this is key. If time is not of the essence (or if the precision of the jump doesn't matter [ie - asteroids]), then simply have the player succeed. An experienced pilot will 100% get it right in a calm, non-threatening, situation.
When it matters is if they're being chased, under a time constraint, or have to make a precise jump in order to dodge an asteroid or black hole or something.
I like this idea a lot, depending on how many threat they roll, perhaps said asteroid field is the secret hideout of some space pirates who don't take too kindly to the PC's discovering their location!