I don't see any need to sweat this stuff unless you see an aircraft alongside you that says "FAA" on it. :wink2:
You have to know the gospel, of course, when you are tested by agents of the FAA, and it is wise to cancel when reported conditions do not meet the legal minimums, but anybody who's flown for a while has had that moment at least once: "am I legal right now? I dunno, but I am OK flying in this."
And if you're a bit conservative like me, you've probably had the converse moment: "I can't believe I'm legal right now; this is scary".
There being no reliable way to know precisely how far you are from any given cloud, or how far towards that obscured horizon you can fly before you can't see the ground or anything beyond your wingtips, what's really important for VFR flight is whether or not you, the PIC, finds the visibility adequate at any given time. That's the spirit of the regs, particularly 91.13, which effectively covers the obvious inability of the FAA to know what sort of conditions you are dealing with at any given moment.
At one time, before IFR plans with radar coverage, even before gyros were commonplace, it was legal to continue as long as you could see the ground ("ground contact" or "contact" flying).
Nowadays, that's forbidden in most VFR situations, but it's perfectly legal to fly VFR over a solid cloud deck or fog, as long as you meet the clearance requirements for the airspace.
Given today's congestion, the early practice would seem unwise, even if you are confident you could recover from a disorientation-related upset as long as you could see the ground. And bailing out when low on fuel on top or unable to maintain control without gyros doesn't work too well today... the plane is more likely to hurt persons or property when it comes down.
But an emergency descent through clouds, or worse yet, into ground-hugging fog, seems even more foolhardy. Yet it is perfectly legal to set yourself up for such a scenario these days... unless it doesn't work out, in which case you might get clobbered with 91.13 (and rightly so, IMHO).
I'm not condoning busting VFR minimums; I'm "just sayin'". The regs don't keep you safe; your judgment keeps you safe.