I am a novice and I'm the first to admit that this is a major undertaking. I will be doing small one to three day events as well as going to the next iba start line. I've been modifying the tiger and planning for better equipment such as a better saddle and lights.
I'm not sure about an auto oiler, I'm under the impression that sticky oil will collect road sand and eat the chain and sprockets. I've been using Teflon dry lubes so that doesn't happen.
I will be studying blogs of riders that have done this and the book referenced earlier in this post. I have lots to learn.