Sometime a better gage than your thumb is to sit on the bike with your full weight and see how much the tires depress, or how large the contact patch becomes. When riding, the danger is that a sharp jab on the tire, like hitting a pothole, will compress the tire all the way to the rim and result in a pinch flat. I assume the tire may see several times your weight in a dynamic condition like that, so you're balancing that possiblity with an adequate contact patch for traction.
Oil is good, grease is better.
2007 Peter Mooney w/S&S couplers/Terry Butterfly
1993 Bridgestone MB-3/Avocet O2 Air 40W
1980 Columbus Frame with 1970 Campy parts
1954 Raleigh 3-speed/Brooks B72