Velvet, of course you are legal at take off, the weather forecast allows for that and the hypothetical operation sounds well equipped (although I like the dual pilot option). Now if I were to investigate a mishap involving this operation and had the opportunity to talk with the surviving pilot, I would have to ask if the weather at the time of the crash was VMC or IMC, how can you tell? You mentioned the moon was sinking and only 28%...can you see it or is it obscured? The overcasts will likely diminish the ability to see the oceans surface at that altitude.
Dewpoint spread isn't much in this hypothetical situation of yours, so let me throw in another variable (just for fun). Since there is no reported visibility for the entire route, then there will likely be no mention of the marine layer 15 miles off shore where some warmer water meets a loving airmass, how long do you think you would be flying above or even in the clouds before you realized you were in IMC conditions? If you have no way of determining the vis or the on scene cloud conditions with the naked eye I might ask how you would call it operating VFR if you can't see the weather for what it is and without the knowledge of what it will be at your destination. Legally, the horizon "angle" doesn't play in the definition of VMC, just clouds and vis. And then your NVG battery light flashes and you suddenly remember you forgot to change out the other one the last time you saw that light...and there are no spare AA's to be had
Blink Blink Blink Blink...are you going to be legal when the NVG's go out? As you said, you can see absolutely nothing.
Good discussion points you bring up, but enforcing the legality of this stuff is impossible unless you run into the cloud police up there, it always seems to come to light after the crash for some reason.
