That looks like it is for a threaded fork. I have never seen a roller bearing headset like that. All the headsets I worked on for threaded forks used loose ball bearings.

The roller bearings are something that you would have to worry about grease, cleanup, etc. Cartridge bearings would allow you to avoid having to carry grease on your trip.

I think you should just use whichever one you prefer. Since I have never worked with a roller bearing headset like that, I can't offer an informed opinion.

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One more thing I should have mentioned in a previous post - S&S couplers come with discs that cover the end of the tube. Some installers use them, some do not. If your couplers have those discs welded to the end of the tube, that means that if water gets into your down tube and possibly top tube, the water can get trapped there and cause localized rust in the downtube and maybe top tube.

Water in heavy rain can get past a headset into a head tube. And most head tubes are drilled so there is an opening into the down tube and top tube, any water in the headtube can therefore get into the downtube. Next time your fork is removed from the head tube, look inside the head tube to see if there are open holes into the top tube and down tube. If so, I suggest you cover those holes with some tape so any water in the head tube can not get into the downtube or top tube. This obviously is more important if you have those discs welded to the ends of the frame tubes at the couplers.