I like what you've done with "Grog Time of Day", Gibb, and thanks for the summary sheet on this. I would definitely say that this song is well attested early on and it's interesting that it survived down to at least 1916. It might be worth checking out fiddle tunes to see if Mr. Chisholm's verse shows up anywhere else.   I was trying to find out something more on Landsman Hay, but it doesn't seem that there is anything available on the net. I was just at the library yesterday and didn't think to check on that one.

I'm wondering if it's possible that what is quoted is really one song rather than two. Could the "Two sisters courted one man," part be the verse and the "Grog tme of day, boys" be the chorus? The quote itself does not really make clear whether we are dealing with two songs or two parts of one song. It just says "And the second:" Hugill does not clarify this.

Two sisters courted one man,
   Oh, huro, my boys,
And they live in the mountains,
   Oh, huro boys, O.

    Grog time of day, boys,
    Grog time of day,
       Huro, my jolly boys,
       Grog time of day.

I've not been able to find anything else resembling the two mountain dwelling sisters, although the two of them courting one man obviously has overtones of the Child ballad "The Two Sisters", which could have been sung in Jamaica, although I know of no record of that. It was a popular ballad and took many different forms such as the widely known Virginia version "The Wind and Rain".