It's interesting to me how different pilots assess risk differently depending on their background.
At work, the pilots I fly with have a wide variety of backgrounds. Some, like me, came up through GA with a lot of time in SE pistons, then twins, then in to the turbines. Some come from the airlines, with the usual GA-training background, but no "real" GA flying. Some come from the military, and while some of those have extensive GA backgrounds too, some have virtually zero GA background.
For instance, one pilot I fly with always comments on how many different models of airplane I have flown (something like 60). I figure that's just pretty normal for a long-time CFI working in owner's airplanes. But his experience amounts to a grand total of 5 different models, and the only piston time he has is the 10 hours in a Seminole so he could get his ATP. The rest is in turbines (I think his military time went T-6, T-1, then AWACS).
Some of these guys don't even have a single-engine rating on their pilot certificate. But all of us are multi-thousand hour, experienced professional pilots.
All this to say, that our risk acceptance is largely dependent on our background. I've flown single-pilot IFR with round gauges and no autopilot for years. Not fun but doable. But you can imagine if a pilot has only ever flown in well-equipped turbine aircraft with all kinds of backup systems, AND a "backup pilot", they would understandably be very concerned about flying IFR in a minimally-equipped single engine airplane by themselves. It IS much riskier than what they're used to, and accepting that level of risk takes time and experience in that environment.
But we see this in ourselves too. The first time you fly IFR with an autopilot, you think it's the greatest thing ever. You probably say something like "man, I'm never flying IFR without an autopilot again!" You probably don't really mean it, but then after a few years of IFR autopilot use, you get used to it, and eventually it resets your risk tolerance. Then the autopilot breaks, and maybe you no longer feel comfortable enough to decide to depart IFR. It isn't even really a matter of the hand-flying skills necessarily, it's simply that your risk tolerance has changed.
People who have never parachuted probably think it's way too risky. But to some who BASE jumps, normal skydiving probably seems pretty ho-hum.
So while I still think the OP's acquaintance is sounding like a pompous jerk, I can see where he's coming from. HE doesn't feel comfortable, and therefore scoffs at anybody else who DOES feel comfortable.