If this is a brand new, never started rebuild, you need to be careful. You don't know anything about it do you? Just read all you can find about new motor startup procedures. You can double check your new filter and it's plumbing. If the motor was rebuilt and then set for a long time, the assembly lube could have migrated down hill somewhat. Oil will start flowing once it starts and I like to see it with valve cover off even though it splashes a little.
FIY RE drill: You need a good drill and it takes a few minutes with a drill, not 45 seconds. It seems like a looooog time for oil to appear. Your oil pressure is good so that's a pretty good thing. Some people like to prime on unknown motors/new motors, it's done all the time and is an indicator of flow and piece of mind. Some say it's an absolute must. You can pour oil all over the valve train too.
Jerry has done this hundreds of times, but this is your first time and the only motor you have. I am squirrely about this stuff also, it's OK.
Ponder these:
http://paceperformance.com/p-3978-engine-start-up-procedure.htmlhttp://www.crankshaftcoalition.com/wiki/How_to_prep_and_start_a_rebuilt_engine
