There's also something called take off angle. A quarter wave antenna has a higher take off angle compared to an antenna with higher gain. The quarter wave will transmit it's signal at a steeper angle off the horizon more than a gain antenna will. An antennas gain is measured by how much signal it will transmit, and receive, across the horizon. If you've ever been in a large city you might have noticed that the police cars, fire trucks, etc., have quarter wave antennas on them. Alot of repeater antennas are located on top of tall buildings, when you're driving amongst the buildings the quarter wave antenna will perform better than a gain antenna. The quarter wave is shooting it's signal higher into space, more so than the gain antenna. If you live in a rural area, like I do, the public safety vehicles use a 5/8 wave gain antenna. That way the signal will be transmitted more across the horizon rather than shot into space and wasted.
There are pros and cons to all types of antennas. Just choose one based on your particular application. If it's for monitoring, and you plan on staying within the geographical area of your monitoring, I would choose the quarter wave. They're less expensive and they're more "friendly" to getting bumped by trees and so forth. Shop Ebay, they have some good deals on commercial brand quarter wave antennas, coax, connectors, etc.