Put the academics to one side just for the moment, and think in practical terms just what the regulations are saying. You need a bolt hole at all times which you can comfortably escape to if your (planned) world starts to implode.
Take that one stage further, and hope for the best, but plan for the worst.
I can recall many moons ago when I was flying up to Sumburgh, Shetlands (LSI)in a Shorts 360, with previous drop offs at Inverness, and Kirkwall.
Planning TAF had LSI as CAVOK all day. Update at INV ~ NOSIG. Latest actual obtained at KOI now giving BKN 007. Uhmm I thought. Shift in the surface wind.
. Arrived to be greeted by 300m FOG.
As the weather up north can be fickle even at the best of times, it kept you on your toes. That combined with VOR approaches at KOI (now ILS) made life somewhat interesting at times. The wind could also be sporty at times