Brad,
Just a wipe around the skirt bottom to get it wet is all.
The rings and cylinder are bone dry untill they make contact with the skirt.
When buttoned down, the cylinder walls above the rings wil be dry.
Chromed, but dry.
Once the crank is turned on starting, the rings will encounter some oil that was transferred by the skirt, and the incoming charge will contact all surfaces. Total distance travelled while not under load and in contact with naked liner is about zero when ya think about it.
The rings contact surface just needs a whisper of film of oil to keep from burnishing the chrome liner.If ya can see a film, it's too thick.
On the big end bearing, after the thing starts, it is only the incoming vapor lubricating, as any volume of significance will be flung off by centrifugal force.
Good 2 stroke oil is amazing stuff, when ya think about how well it works at so little volume.
I probably swapped out 100 sets of rings, and pistons every 4 races back then, and never had an issue except with some bad factory slugs.
Before the Kawasaki Chrome cylinders, I ran all YZ's with Iron Liners and we did splooge things real well with the old Castrol or golden Spectro.
Had a couple get glazed, and busted rings a couple times.
I ain't a pro builder, but when the Team Green Wrench say's "Do this, this is how we set up Wardy and Goat" that's what I do...did...LOL!!
Stay safe!
Dingeryote