To retract, or not to retract, that is the question..

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Personal preference is to leave the gear extended IF there is an area ahead that would accommodate a forced landing - at least until at such a height that I could get the gear extended again if I had retracted it and subsequently suffered an engine failure. The reasoning is that most aircraft crash better if the impact is taken by the landing gear and not belly-up.

 

Of course there are exceptions, e.g. where obstacle clearance is critical (but only retract if the doors etc don't make drag worse during the cycle - see other comments about Cessnas etc). Also, taking off over water, where you most certainly will want the gear up if you have to ditch.