Two tips--I too have had Flight loose the brake command on my joystick, but I had programmed a button for "parking brakes", and that continues to work. I found that clicking that command deploys a moderate braking effect, but for gently slow down, just click again to coast, then again if more slowing is required. If your joystick doesn't allow for normal brakes, the parking brake workaround may be sufficient. Secondly, for newbies who are having trouble in some of the landing challenges, beware most setups are not straight in approaches, so just aiming for the yellow diamond is useless. Rather, the simulation doesn't seem to care if you scope out the runway, circle it once or twice, notice surroundings, trees to aim toward and so on, then notice the wind direction indicator and approach the airport against the wind. Most challenges seem to also add a cross-wind element, so that indicator is pretty helpful. I confess to crashing the Stearman a few times on some of these challeges even using this tip, so be patient!

Yup the landing challenges, especially on the Icon, tend to set you up much to close to the airport for a simple straight-in approach. Pro-tip for the Icon landing challenge number 6, you can still get gold if you end up beaching your Icon :D.I too have bent a few Stearmans doing the landing challenge.