I would not use an oiler anywhere in the line. They are typically used for stationary machinery, oil in the line will drive you nuts if try to use that air to paint with, oil the individual tools by themselves not the line.
I would run unregulated air in the line, this will allow full compressor output at any point in the shop, important when using a heavy impact or other air eating tool. I use plug in regulators and use them when I need them, about the only place I do use them is in front of a paint gun or something like a die grinder where I want to control the speed. The thing to remember about regulators is that they will give you some cfm loss even running wide open so it's usually better to use them only where/when you need them.
I would make the first run of pipe from the compressor run up hill away from the compressor, a lot of the moisture will condense in this first section and slowly run back into the compressor, in which hopefully you are installing an automatic tank drain. Then further down the line add a moisture filter, one large enough to handle the CFM of the compressor, check some place like mcmaster.com or granger for an industrial model.
Otherwise with your plan and the advice you got above sounds like you are good to go!