A drip leg is mainly for gas lines at very low pressures. Won't accomplish anything with a high flow/high pressure system like this. It never hurts to have another filter/water separator immediately after the compressor.
The Milton regulators I used say the same thing on them about being rated for 150 psi, but the three on my system have been on there since 2005 when I installed it all and nothing has ever failed and I have had zero problems with them. Just have to drain the water separator on them periodically. The regulators are made to where they won't let you crank the output pressure up to but about 120 psi max. I have had them there a couple of time trying to get a large, rusty nut off of something on a truck with an air impact wrench.
Another hint--put a ball valve immediately before each of your regulators. That way you can turn it off easily, let the air out of your hose, and drain the water separator without having to turn it off back at the tank and drain the pressure from all your piping just to drain the water separator.
The only thing I would do different in my system at this point is I wish I had used the Milton high-flow quick connects that are out now. I don't remember the letter designation for them, but you can get them at Northern Tool also. I have the M-style like I have used for years on other systems, but they are only about 1/4" inside diameter and are a big restriction in my system. It hurts me when I try to use my 3/4" drive impact.
Also, I highly recommend you go by a hydraulic shop and have them make you up a length of high pressure 3/4" hose with crimped, swivel pipe thread ends on it to connect between the compressor and the piping. Alot of vibration in that compressor and you don't want that going into the piping like it will if you hard pipe straight to the compressor.
I also found some rubber vibration isolator mounts that were used under a diesel engine in a generator and mounted them between the compressor feet and a wood frame I made. Makes it quieter, keeps the vibration out of the floor, and keeps it from wanting to walk on the floor when it is running.