"But I noticed that the rifle bullet would not "sit" on top/in the case on its own. However, if I hold it there and pull the handle, it seats the bullet to the correct depth. Is that what others have to do?"
I don't use flat based bullets, so no. Boat tails sit in really nicely. Flat based bullets are a PITA when you're used to pistols and boat tailed rifle bullets.
For your first question, I use a Dillon 550 for my match rifle loads. I load them like Chemistry does, just lay them about, give them a squirt or two, shake, and maybe one more squirt (roughly three squirts for about 200-300 cases.) Load 'em up...it'll on;y take an hour.