Wire bypass/override switches in a landing gear circuit
Let me address a couple things as a pilot...


  Why? Well, for example, if the pressure switch in the gear up part of the circuit should fail, I can still get the gear to retract by activating the override push button.


This is a big no-no as a pilot. The last thing you want to do is to bypass something that is failing. If your gear doesn't retract, leave it down, enter the pattern and land. Fixing issues on the ground is infinitely better than trying to fix/diagnose them in the air. Eastern Air Flight 401 was caused by the pilots fixation on a faulty gear light, losing situational awareness and crashing. 


  Another example would be on a lengthy cross country at high altitude where the colder temps cause the pressure that holds the gear up to fall enough to slow me down (because of drooping gear doors), but not enough to activate the pump automatically. In this example activating the gear up override/bypass switch manually will bring the pressure and the drooping doors back up.


You need to design your aircraft such that these things don't happen. Typically aircraft use pressure switches not analog sensors, and once they are up they are in a "locked" position. The gear system hydraulics rotate cam locks (or other devices) such that a loss of hydraulic pressure doesn't cause inadvertent gear extension. 

As I said in the comments, you need to have a back-up system that is either a manual release (rotates the cam shafts and allows the gear to gravity drop) or a manual pump in a secondary hydraulic system. Do not use bypasses.