Howdy Back Frank:
Q- "When I replace the seals and push the umbrella seals down what keeps them from riding up on the stem again later?"
A- The top of the valve stem boss is as cast, so it is somewhat irregular. The seals fit tightly over and with a good bit of grip from the rough surface. The valve stems pass through the guides in a hole that has a flat contact surface on the inside. That smooth, flat surface against the smooth, shinny surface of the valve stem allows the valve to pass through while the seals grip on the guide boss holds tight. Time, heat cycles and wear slowly degrade the seals.
Q- "Should I clean the mating surface between the head and the seal dry and clean (or )put a small amount of oil on the seal and then press the seal down?"
A- Yes, Clean the "Bee hive shaped" top of the stem boss and add a drop of oil to the inside of the ring seal that the valve stem passes through. When pressing the seal down take note that it is not cocked off center. take a minute to make sure each seal is completely seated and centered on each boss.
FYI- on startup, watch the oil as it seeps from each rocker, from back to front. It should take no more then a minute until all rockers are receiving oil. The flow of oil over the rockers, springs, valve stems and seals is what keeps the top end lubricated and cooled. THe oil comes up from the rear staunchion, passes through the rocker shaft to each rocker and then out to the valve assembly. There is a good sticky at the top of this forum on the oiling system on the top end and how to clean it up and improve on it.
Keep us posted on your progress.
Adios, David