Colleagues,
I challenge you to have a "pop" on take off, especially near to Vr, get airborne, get the "positive climb" call and NOT call for the gear up. It's ingrained by SOP and is very difficult to override.
Try leaving the gear out on take off from Johannesburg/Addis/Entebbe or any other high altitude airport and you could be asking for a lot of trouble. In the absence of positive signs of damage to the airframe/other systems, get the gear up. If there are signs of control damage, chances are you don't want to be juggling with that and performance issues with the gear down either. However, that's subjective.
Fly the aircraft, get away from the ground and safe, then work it out. Assess and manage.
Sure you waste some gas and delay your passengers but you don't take the chance that the gear would hang up in the well when you tried to put it down.
So if the gear's going to hang up: A - How do you know?
B - Why be half way when you could be at destination at the lower wieght?
If you are worried about it, you've got longer to think about problems and solutions, look at checklists etc.
If there are no other factors, landing at destination is as safe and commercially sensible.