Converting from 44.1 to 96 is an impossible premise for improvement because it's a 44.1k signal to begin with. The only benefit I can see of 96k is this: Every digital conversion will produce some artifacts. If you get enough tracks together, there can be some awkward manufactured overtones as a result of the combination of all the converted signals. You don't have that with analog. So I think 96k would reduce that possibility in a very large multitrack session, where a lot of things are doubled. Like if you had 10 guitar tracks, a drum loop + real drums, multiple vocals, etc. all with seperate effects tracks, you might hear a difference in your final master.
Even then, worrying about 96k and 24 bit is a waste of time IMO. Especially on a Boss or Roland box. That's so laughable, because you are inputing through their consumer grade preamps, EQ, and digital effects processing. (including the essential compression) If you're using COSM on anything, guitars, mics, whatever, then you're a slave to that level of sound quality, regardless of the sample rate or bit depth. Not that the Roland boxes sound bad, because they don't. They sound good. But the high conversion specs are simply marketing hype on those boxes, unless you're bypassing all the fancy features and using pro grade outboard gear. In that case you wouldn't be buying the Roland box. You'd get a stand alone multitracker, or you'd stay on the computer.