When to retract the gear?

[Rickskymaster]

If it depends on how many engines you have running, what happens if you retract upon having positive VSI, both engines are running, gear is in transition and then engine failure.
The gear doors are open, gear is somewhere in coming up.
It would seem safer to wait until 500 or 1000 feet to retract.
I would love to hear everyone's opinior on this.

Rick