I believe that Gaines Landing was on the Mississippi River. I'm relatively sure that it wasn't one of the landings on the Saline. If so, it's quite possible that the original road is lost to time but might have followed the path of the present day highway from Monticello to Dermott. I'm relatively sure that Gaines Landing and Gaines Street have no connection other than a cooincidence in the names. As to the topography of Rough and Ready Hill not being suitable to drilling troops, I can see your point. But there would have been many areas of relatively flat land in the immediate vicinity. If they were actually over in the Mississippi River Delta (eastern Drew County is in the Delta), then they would have had lots of flat, open land on which to drill. However, whenever it rained, their camp would probably have turned into a bog. Mosquitoes are also more of a problem over there which would have also increased the risk of malaria. So - i'm trying to use logic here - if I were picking the site back then, I would want an area that is relatively flat but with good drainage and few mosquitoes. I would also want a source of fresh water. As such, that opens up quite a few possibilities in the immediate area of Rough and Ready. Namely, there was a confederate supply depot on present day College Street in Monticello. The area between the depot and the hill meets many of these requirements. The ground is relatively flat with good drainage, it isn't far at all from Rough and Ready (15-20 minute march) and there would be numerous sources of water. Namely, the fresh water spring on the slope of Rough and Ready as well as the numerous water wells and cisterns that would have been found in Monticello. I'll tap into the Monticello network and see if anybody knows anything there. I realize that I haven't been of much help.