How do I get the oil in ...
Before you run out and buy a pump oil can, you can use any thing with a small nozzle. I would suggest you buy a small plastic bottle with a pointed nozzle like an eye drops bottle. It will work better than the oil can. As 64SS409 mentioned it takes very little oil. Add oil until it just fills up and let it go until the engine oil change.
I have a bottle like that I use to oil my air tools. In fact, after your question, I am going to buy another bottle for motor oil. My pumper can retire since I use it so little the oil left in in is probably as old as me and is probably turning to grease...
One last point, the oilers are located on top of the generator at the front and rear of the generator (to feed both bearings) and have a spring loaded flip cap just in case you are not familiar with oilers.
Thanks for the question since I was religious with oiling my brothers, 49, 55's, 57 and 61's when I was young, but cannot remember the last time I checked my 61's...