Actually, black paint retains heat better than other colors. Lighter colors such as engine greys or silver do a much better job of disappating heat (and radial engines generate a lot of heat). You have to remember that a/c cylinders are made in two parts and screwed together under heat & pressure, w/the upper 1/2 (the head) is made out of aluminum alloy, while the lower 1/2 (the barrel) is made out of steel. The head is rarely painted while the barrel is usually painted w/grey or aluminum paint to prevent corrosion (rust). (sometime late in the war, the Navy and P&W developed a method to spray a thin layer of molten aluminum over the exterior of a cylinder to aid in heat dissapation which made the cylinder appear silver overall)
Most of the black you do see on a radial cylinder is actually the baffeling which is bolted to the cylinder in order to direct and control airflow around the sides and top of the cylinder for cooling. (they're soooo much fun to remove and replace during a cylinder change). I usually paint 3/4 of the cylinder around the sides w/black and the top of the cylinder black to represent the baffling with a vertical silver stripe on the front 1/4 of the cylinder to represent the part of the actual cylinder that can be seen. After that's dried a couple of days I apply a very thin wash of black to the silver area to accent the cooling fins (which are grossly over scale on most models).
As far as oil leakage goes, most of the stains will be aft of the engine where the airflow blows the oil in flightand on the lower part of the cowl and nacelle when the a/c is sitting on the ground. Depending on the condition of the engine and the amount of maintenance performed, the oil stains can range to very light, to very heavy (I once saw an old DC-6 which had been sitting on the ground in Kansas City for two days - it had a puddle of oil under the #1 engine that was a good 12 feet in diameter, an inch deep and was still growing visibly from the oil leaking out of the cowling and off the wing - the crew came out, added about 15 gallons to the oil reservoir, cranked her up and took off!)
Remember the basic rule of thumb of the radial - If it ain't leaking oil, it's out of oil