It Has Arrived! Pro-oiler.

On a related theme I watched the MCN long term test on the Tiger Sport 800 yesterday and it came out very well. Neevesy was asking the long termer what she thought of the bike and one of the very few negatives was the Scottoiler she'd had fitted which covered the back of the bike with oil, yet she'd had to have new chain and sprockets fitted at around 10k miles which seemed strange so hopefully yours will work better. I could be smug and say those like myself and @learningtofly don't have this chain issue thing but it'd only fall on stoney ground

 

The method you describe where for chains of a simple structure, comprising of rollers, plates, and pins. They are very simple and do work reasonably well, the drawback is metal-on-metal contact and lubricant cannot be easily retained by the chain, and they have a tendency to trap dirt and debris around the pin, hence the chain required regular maintenance, and they broke frequently, hence why they have a split pin arrangement. Thankfully the development of the O-ring chain early in 1970, which added a rubber insert between the inner and outer link plates to act as seals to keep dust and debris out, retain better lubrication, and reduce metal on metal friction. This helps to solve many of the maintenance issues experienced by non-O-ring chains. More recently, X-ring chains have come onto the market. These are similar to O-ring chains, but they have a different insert profile, which offers less stress and deformation retaining a better profile. The O-ring chains are great for regular road riding, however if you like a few track days and some spirited road riding the X-ring is in my view a better option.
With regards to lubricating the chain as riders we all have our own method of cleaning and lubricating the chain. Personally I would never use either a vacuum or electronic chain oiler, simply due to the fact that they can and do malfunction. This can result in oil deposited on the rear tyre and nobody wants that. Also the chain still requires regular cleaning, dust and debris still get trapped in the chain no matter what lubrication is used, so if left the chain will deteriorate more rapidly if not cleaned. Also the electronic/vacuum type only lubricates the centre chain rollers, it leaves the side plates untreated, what happens is rust appears on both the side plates, and if not cleaned off early enough will eat into those side plates. For myself I will stick with cleaning my chain with chain monkey, and lube it with the same brand chain wax. I have tried all manner of cleaning and lubrication products over the years, if I come across something better I will use that, but for the last few years it has served me well. And my OEM chain and sprockets are still looking good. But come the time for them to be changed, and it will be a quality X-Ring Gold chain and sprockets for me.