I'm just setting up my piping system now (that was one project for today actually). I'm using 3/4" black pipe for the main line (horizontal and initial riser off the compressor) and 1/2" black pipe for the drops. And, yes, it does get expensive...
I'm more or less following a mix of:
1.
http://www.tptools.com/statictext/airline-piping-diagram.pdf
2. The free tear-off at the Home Depot by the air tool fittings
3. Common sense.
For your specific situation, I would run the air dry (oil-free, it would still have water in it of course) in the main piping system and place two in-line oilers, one at each "half" outlet. (Two outlets at each location, one before and one after the oiler.) Another good alternative it to run an oiled line to the center point and two outlets to the workbench and resign yourself to using flexible lines if you want an oil-free line off the workbench. Personally, I don't think the in-line oilers are particular good when they are too far from the tools as there's too much wall friction to help pull the oil out of the air, so I'd be inclined to multiple in-line oilers anyway.
(Whatever you do, don't use PVC!!! Use a metal pipe of some sort, slope the main line for condensation clearing, and take your drops off "up" to minimize the water you get in them. The metal pipe will help cool the air, remove condensation and PVC is just plain unsafe in this application! Slope the main line down away from the compressor to a drain drop. 6" in 50ft is probably enough slope.)
For four drops and 50' or so of horizontal run (it's an airplane hangar and car repair shop), I'm looking at around $350 for the whole piping system, but it's done right and it will be so nice to not have to trip over air lines for the next 20 years.
---Jim