You're suggesting that an airplane in which the brakes might need to be checked or "pumped up" prior to landing is experiencing a malfunction or poor maintenance. Have you ever landed an aircraft which has no steering capability other than brakes on a short field requiring maximum braking right off the bat, and then had the aircraft attempt to go right or left on that narrow short little runway because one brake acted more effectively than the other?
Perhaps Because of air in the system, perhaps because two different actuating cylinders are used, each in their own state of wear, perhaps because of small differences in brake depth, or different temperatures of expander tube material?
Don't make the assumption that mererly because a cylinder may require or could use more than one application to ensure immediate response, that it's a sign of poor maintenance or even equipment condition. It may not be. In fact, it may be inherent to the type of brake. Some brake systems intentionally leave air in the assembly for expansion purposes, and may require an additinoal application to ensure response. Ice present on the disc assembly may need to be broken. Cold weather may mean a different rate of bypass or different sealing properties in the cylinder or different movement properties on the brake puck.
Do you know for certain you're "testing" the brakes when you apply them? Some systems bypass once the weight is off the wheels. How well do you know your system? If you're flying a cherokee, then you've got direct pressure between each cylinder and it's respective brake assembly...very simple, but you can still experience a difference in feel and pressure between them. This can be especially true if one has experienced a malfunction and been replaced with new, when the other hasn't. This doesn't necessarily mean poor maintenance or equipment, or a need to visit the shop. It may mean, operationally for you as the pilot, the need to ensure equal functioning prior to landing on a narrow short runway if braking and directional control may be issues.
Conversely, if you have a leaking brake or hydraulic system, pumping may mean you're pumping the last of your fluid overboard. Use care.