Yes Glen Dave's right, the first stage on up grading the oiling system is to drill out the stock 3/8th diameter pickup hole to take a 1/2" hemi pick-up. As for big oil pans , the more oil the better within reason, but you must make sure you have a correctly designed pan for you application, drag cars have different requiremnets to street driven ones.
The next stage after the uprated hemi pick-up is to go to an external oiling system, this uses an adaptor block that bolts between your block and oil pump and takes oil from a big pick-up inside the pan and routes it outside via a large diameter braided line. You can use a good quality stock style pump here, a 'Mopar' high volume , high pressure pump works good on engines up to 7500+ RPM. I had one on an engine making well over 750HP, that ran for many runs down the track and never agve a problem.
After this you would go to a swinging pick-up design which actually moves back in the pan to keep the pick-up in the oil as the car accellerates hard, generally at this point you would switch to a dual line setup on the inlet side of the pump and this is where the big after market oil pumps are used. The Miloden race pump is OK, but an old design, it's actually made for a Ford! And they suffer from a lack of self priming, which is a big problem if you need to get the car started in a hurry.
There are several companies now producing billet pumps, I use the RBRE on and that works fine on my stroker Hemi, Indy make them, a company in California called Titan also makes them.
You could also run a crank driven oil pump either single or multi stage , but this is all really race only.
Although my smallblock uses a single stage Moroso pump fed from a fixed pick-up in a modifed stock style pan. That makes 80PSI all the time and never drops below 55 unless you switch the engine off.
The biggest problem with keeping oil in the motor is generally the stock oil pan, unfortunately with the K memeber in the way there is only so much that you can do. A graphic demonstration of this is seen on the Superstock hemi A bodies that had the draglink going THROUGH the oil pan, now to say these things had very little steering lock is an understatement!
I had a custom ally on for my dart and it had to go back to the manufacturer to be modified so I could turn the steering wheel more than half a turn