Whooooppss, gotta counter this statement. All of my comments below are in regards to steel cable.
The Roller Fairlead will do nothing to guide the cable when spooling. That will be determined by the direction of pull. It's inevitable that the cable will spool tangled and crossed over when used. Don't worry about that too much while pulling unless it piles up on one end of the drum so much that it starts rubbing on the winch structure or fairlead. When you park the vehicle for the day it's very important that you unroll the cable and respool the cable manually, guiding the cable back and forth across the drum so that it is not crossed over itself and will be ready for use the next use without kinks. I do this by hooking the cable hook to a stationary object, put the winch in freespool and back the vehicle away from the hook until I have unrolled down to a good straight spool. Then I engage the winch and start spooling in cable while dragging the vehicle and guiding the cable back and forth across the spool. On my ATVs I do that while sitting on them and watching the cable spool. On my Jeeps I use my remote control and guide the cable by hand while spooling. When I'm done the cable is smoothly spooled without any kinks or crossovers.
As for oiling the cable. I do not oil my cables. I wash them if they get packed with dirt/mud, leaving them unspooled and stretched taut until dry, then respool, guiding the cable evenly on the drum. If you oil your cable it will attract dust, sand, dirt, etc., which will become embedded in the cable and then start grinding on the cable strands every time you use it, eventually weakening the cable.
As was stated above, use a Roller Fairlead for steel cable and a Hawse Fairlead for synthetic cable. If you try to use a Roller Fairlead on synthetic cable it will get pinched between the rollers and damage the cable. If you use a Hawse Fairlead on steel cable, the cable will wear grooves in the Fairlead and then those grooves will start cutting strands of the steel cable, weakening it until it fails. Properly use and care for your winch cable and it will give you years and years of service.