DFC,
Do you carry IFR charts on VFR flights? - No? but even with an IR or IMC the flight becomes illegal on entering cloud because you do not have the appropriate charts to get to a safe destination for sure. Never mind illegal, think practicalities - how do you naviagte to suitable approach minima!
Yes, I always have the relevant AIDU FLIPs with IAPs; yes, I always plan my VFR flights with MSA for each leg; I always carry a half-mil chart which has MEF figures for each square; most of my VFR routes use VORs as waypoints when they can; I always have a GPS switched on and the route programmed in; and I'm always outside CAS, and 90% of the time talking to someone who
can provide a radar service.
So if I need to go IFR, it's no big drama: climb to MSA; tell the controller I'm now in IMC and need a RIS/RAS; sort out the routing (divert if necessary); get out the approach chart; and get on with it. Again, 95% of the time I re-enter VMC before the approach anyway so make a visual approach. Really not that much of a big deal, as long as you prepared the VFR flight properly.
Of course, if your VFR flight wasn't prepared, you relied on GPS for navigation, you didn't work out MSA, you left the charts at home, and you didn't use your radio at all, you'd be in more trouble; but you'd deserve to be, frankly.
Tim