Cows - I'm not sure it matters whether he had 100 hrs or 10,000 or whether he was PPL orATPLIR - it appears he planned to make a flight in poor weather, with few options, under self -imposed pressure to make a family gathering. It was his decision-making process that was at fault and, as we have discussed frequently, it is not just low-time pilots who make crap decisions.
Scardy - what you describe is flying supervision, something that may be available if you work for a company with experienced pilots but is generally sadly lacking in private flying. Having someone to look at your plan with a fresh pair of eyes and no self-imposed pressures and who is prepared to be honest about your ability to perform the flight in the prevailing conditions can be the difference between life and death.