You know the Scott oiler is always oiling the chain, so you really can't over oil it...provided you aren't wasting or getting the oil on your tires, etc. Some people oil after every ride. Others every couple hundred miles. If you ride in rain or dirt, more often. I use the same cheap oil to clean the chain, by spraying it, then wipe off all the excess I can, and I oil every 200 miles or so. I clean off the rear sprocket at the same time I oil the chain. I prefer to just move my bike and do a section at a time rather than use a stand and have the wheels moving because of the added danger of that, but I think most people use the rear stand. Just watch your fingers and make sure you move the wheel so the chain is moving away from the sprocket. At a 200-mile cleaining/lubricating schedule, my chains always look brand new. I wipe the excess off with a microfiber cloth. Several YouTube videos on this.