Well Scottoiler have now released a twin nozzle applicator which lubes both sides of the sprocket so obviously they believe there is a case for applying to both sides (or they just needed a new thing to sell
). All I can say is that, if you use the thin oil they specify, it gets pretty much everywhere you can imagine until you get the flow rate just right. The theory is that the oil is applied at the bottom of the sprocket and then centrifugal force pulls it through the chain and gradually flings it into your chain guard along with any grit and rubbish off the road.
All I can say is after a bit of fettling of flow rate, mine seems to keep the whole chain slippery and fairly clean without coating the entire rear end of the bike in oil. Let's face it, you're only really oiling the o/x rings inside the side plates and the oil definitely finds both of those easily enough.
Be prepared to whip your chain guard off every now and again though to wipe away the thick gummy mix of oil and road dirt from the underside.