It's a means of mitigating risk. On the first flight there is a large list of untested things. Raising the gear adds one thing to the list, and it's best to let the list get a bit shorter before you start making additions.
Hypothetical example:
For instance, maybe you can't get the flaps to extend on landing on the first flight. If the gear also didn't lower you would have to do a wheels up landing at a higher speed than with the flaps down. If you had waited until the flaps were tested and working before testing the gear, you could have done that gear up landing at the lower, safer speed.