Pilots of planes with CAPS are (now) taught to pull the chute if anything goes wrong inside the profile (low enough speed, far enough above ground) where the chute is designed to work. The aeroplane is insured, you can buy a new one. Even if the pilot and all passengers are insured you can't buy new ones.

They changed this because it turns out that the same phenomenon that leads to private pilots taking undue risks in the rest of flight ("Get-there-itis") also makes them reluctant to pull the chute even when it's clearly their best option. Pilots who clearly couldn't reach a safe landing spot, yet had working CAPS would dig themselves (and their passengers) a grave rather than just pull the handle. So teaching them to start by assuming they'll pull the chute and only then considering whether there are other options reduces the fatality rate.

That's exactly what I wondered about. How one parachute and two crew can lead everybody uninjured.