We'll start with the common-sense, easy ones first.
Windage tray. Duh, right? Well, make sure yours has the vents opened wide enough. Most of the new ones I've seen from MP have the vents barely opened. They need to be open at least 3/8".
High-volume oil pump. I usually don't worry about these on small-blocks but with the B/RB's rather foolish oiling layout (we'll get to that) and ginormassive bearings, it's more of a concern. Don't go for high pressure, just high volume.
Capacity, capacity, capacity. More is always gooder, via added side kickouts or depth--just make sure the pickup shield either contacts the bottom of the pan when your done, or is within 1/16" of it. Steal the kid's Play-Doh to verify this.
Install acceleration baffles in the sump to make sure the oil stays at the pickup. If you use an aftermarket pan it will likely have these, but you can do it to a stock pan if you'd like. Just look at pictures of the aftermarket pans you're too cheap to buy, ya fuckin' chiseler.
Make sure all crank oiling holes are clean, unobstructed, and chamfered. Drill through them if necessary to clear obstructions. If you're running full-floating wrist pins, drill a 1/32" hole dead center from the top of the rod to the pin bore, then slightly chamfer that hole at the top of the rod. Make a fixture for this so it's straight and perpendicular to the pin in all directions so the path is short as possible. If you're not running floating pins, don't bother--it does nothing, and besides, you're not really trying anyhow.
Smooth any drainback areas with a die grinder and sandpaper rolls. Oil that's stuck to rough-cast surfaces ain't doing any lubricating or pressurizing. This would include the outside area of the heads "south" of the valve springs as well as the lifter valley. Some guys like to paint these areas with a coating like Glyptal to speed the oil's return even further, but there's some validity to the point that coatings insulate the iron from the oil's cooling effect. I don't think there's a wrong decision here.
No one, to my knowledge, has ever considered an oil cooler a bad idea. This not only increases oil life, it also takes some workload off the cooling system, which is probably a spectacular idea considering the space limitations for a radiator in an A-body. Every degree counts! Any external hoses for a cooler must be rated for engine oil, 100PSI or greater @ 300°F. Do not use heater hose, fuel hose, transmission hose, power-steering hose, etc. They will work for awhile and look perfect right up until they blow apart and pump out six quarts of oil faster than you can reach the key.
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That's all that's really necessary for a typical "street" big-block with a six-grand-ish shift point, meaning it won't be spending any real time up yonder. If you're gonna spin the tits off it (6,500+ shift points) there are more mods you can make, such as...
The first and most-obvious is also not a terrible idea on a street engine, if you can do it: Drill and tap the block for a 1/2"NPT Hemi oil pickup and pan. I'm not sure if the Hemi pickup works with any other pans, nor if the Hemi pan fits an A-body. There are also aftermarket-specific 1/2" pickups. I'm sure some research can uncover the needed information. Any restriction on the pickup side is more than twice as bad as it is on the pressure side, so this is the foremost necessary mod. Be forewarned: Due to core shift, not all blocks are keen to have this done. If your block looks thin around the outside of the stock pickup threads, it's very easy to crack it attempting this mod. Grab a 1/2"NPT pipe plug before you buy anything and compare it to the threaded end of the stock 3/8"NPT pickup. It's a lot bigger--more than just 1/8"! If you crack the block attempting this, it's easier to find a new block than it is to fix it.
Get a long-ass 9/32" drill bit and drill the main bearings' oil feeds up to the passenger's side cam galley. We're talking a minimum 8" long bit here that will drill cast iron--not exactly standard hardware-store fare. Take your time; a bit like that is easy to snap. In fact, any straight pressure passage that you can drill straight through, you should, oversizing by ~1/32". Don't go nuts.
Milodon dual-pickup pan and pump. Absolutely the hot setup short of a dry sump. Not cheap, even used. It can be duplicated at home, but you should either have parts to copy or a shitload of very-clear, very-concise photos. I'd suggest scouring swap meets for complete used setups.
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One less-popular (but quite effective) trick I did on my 440 was to drill and tap a 1/4"NPT hole in the top of the main oil passage behind the timing cover and install a fitting to convert it to a 3/8" inverted flare connection (fuel line). You're going to want a cam and gear installed for this procedure, because clearance is at a premium for this mod--you're gonna end up behind the cam gear at some point. Next, drill a hole in the front block bulkhead nearby, making sure it's large enough to pass a line nut through. In the driver's side lifter galley between the #1 and #3 lifter pairs, clear of the lifter bore, drill/tap another 1/2"NPT hole that faces straight up, and install another inverted flare adapter. Flare one end of your 3/8" hard line, install the gear-side line nut, and bend up a hard line that runs from one fitting to the other perfectly. Easy? You wish. You'll almost certainly have to pull the line back out of the engine to flare the cam-galley side, which is why the hole in the block needs to clear the nut.
What, you ax, is the purpose of this line? Well, it's like this: The B/RB oiling system has "camshaft priority" oiling, to reduce customer complaints of valvetrain noise at startup, way back when they were new. Because of this, the main bearings are fed from the cam galleys, and the passenger's side cam galley is the what the oil pump feeds directly. So, at startup, the oil has to travel from the pump, down the RH oil galley, around the back of the block, and all the way forward to the #1 exhaust lifter before any pressure will get to the main bearings. Yes, the feeds for the main are on the passenger's side, but oil just trickles down them until the (large) cam galleys are both full of pressurized oil. The hard line splits the flow off into the LH lifter galley immediately, so the pressurizes oil meets itself back by the oil-pressure sender fitting. Oil pressure reaches the mains twice as fast.
I used to have pictures of this mod, but I'll be roped if I can find 'em now. I'm not gonna lie, it's not exactly a picnic. In fact, it sucks. All your fittings need to be steel (no brass). Use pipe dope (not tape!) on the NPT threads. Pieces of teflon tape racing through your oil system are not a good thing. Also, you need to pressurize the block with the intake, timing cover, and cam gear missing to verify that it does not leak. If it leaks, make it stop. Leaks around the inverted-flare nuts cannot be fixed by any method other than re-bending the line. The inverted flare isn't seating correctly, and no amount of pipe dope, silicone sealant, anaerobic adhesive or anything else will seal it. Think "brake lines" here. There is no such thing as an "acceptable" leak.
What really sucks is you have to do this mod with the block bare, prior to cleaning for final assembly because of metal chips, etc. but you can't actually test for leaks until the engine's assembled. If it leaks, your heart wrenches being so close to buttoning it up and having to fuck with that stupid line until it doesn't leak anymore.
And now you know why it's not all that popular. It's a pain in the ass, but your oil pressure needle springs to life like a teenage boner in sweatpants while standing at the chalkboard.