The "red flag" is easy to avoid. That said I agree with those who point out risks. I do check computers fairly regularly in order to avoid hassles with security when I have several and to avoid having very cumbersome carryon bags as well. I never ever get insurance or specify the value because I do think that to be a 'red flag'. I don't recommend it, but checking computers is far from the riskiest thing one might do. It may be stupid, but relative to what? I understand the risks and accept them. I'd never check them transiting LHR, for example, where I've never had a bag make a successful connection. In most places I just accept the risks and go for convenience.