Kemble noted a similar song for around a similar time. This again does not contain "hi-lo", but it is otherwise comparable.

1863        Kemble, Frances, Anne. _Journal of a Residence on a Georgia Plantation in 1838-1839._ New York: Harper and Brothers.

So it's circa 1838-39. The setting is a boat trip across the Altamaha River from the Georgia coast to the St. Simon's island.

…and as the boat pushed off, and the steersman took her into the stream, the men at the oars set up a chorus, which they continued to chant in unison with each other, and in time with their stroke,...To one, an extremely pretty, plaintive, and original air, there was but one line, which was repeated with a sort of wailing chorus—

"Oh! my massa told me, there's no grass in Georgia."

Upon inquiring the meaning of which, I was told it was supposed to be the lamentation of a slave from one of the more northerly states, Virginia or Carolina, where the labor of hoeing the weeds, or grass as they call it, is not nearly so severe as here, in the rice and cotton lands of Georgia. Another very pretty and pathetic tune began with words that seemed to promise something sentimental—
   
"Fare you well, and good-by, oh, oh!
I'm goin' away to leave you, oh, oh!"

"Jenny gone away" is also mentioned here, putting that possible antecedent to "Tom's Gone to Hilo" in the same cultural context and repertory.