One factor for your decision is that rope technology has come a long way since our Cherubini's were built. For a given diameter, even for the basic yacht quality line (like sta-set), stretch and breaking strength is now much better than it used to be. The Hunter rigging sheet that came with the my 1980 H36 when it was new (the PO's managed to keep it in the documentation!) specifies 1/2 - 9/16" for the mainsheet halyard. When I replaced mine a few years ago, West Marine had a too-good-to-miss closeout on a hi-tech vectran/polyester type line. At 3/8" it had less stretch and higher breaking strength than (say) sta-set at 1/2". So you might give consideration that there's no need to maintain the original 1982 manufacturer's recommendation. Instead you could look to a manufacturer's recommendation for a 2009 cruising boat with about the same height mast.
Larger diameter does lend a bit more grip when hand pulling, which as Paul F commented some find to be easier on the hands. But hoisting is usually only a once a day event for a mainsail.
Does the halyard on your boat lead to a self-tailing winch? If so, 5/16" might be too small for the jaws to grip well . Or if its a small ST winch, anything bigger than about 7/16" might be too large.
One advantage of the smaller diameter that I found is less resisistance as the rope bends around the sheeves and blocks. With the 3/8" halyard, I now have no trouble hoisting my mainsail all the way up by hand, whereas it was an effort with the old stiff larger diameter previous line. I wish I had known about the easier bending characteristics when I replaced my mainsheet line. It had been 1/2" which also was a struggle to fit into the jaws of the mainsheet dedicated ST winch. (I still don't understand how the previous owners managed.) I replaced with 7/16". I think that the smaller 3/8" diameter would have resulted in a smoother pull through the 6:1 purchase blocks + 2 routing blocks that mainsheet feeds through on its way back to the cockpit. I have no trouble with the feel of the the 3/8" for my halyard and I think it would feel ok also for the continously used mainsheet. Next time, I'll move down to 3/8" for the mainsheet .... just too bad that my 7/16" still has quite a fews years of good life left.