Dr. Whitcomb did some research that says that most of the root branching occurs in the first 4 inches above the prune. It is not exact. So the idea is to pick a container that has room for about 4" of growth on all sides of the existing root ball from the previous container. 1 gal containers are a bit on the small side when going from 18s and 3 gal are a little on the large side. I found that I get the fastest growth by using both, but it is more work to do 2 transplants.
I have planted in the field from one gal containers. Most of the trees survive and some of them will thrive. If I wait until the roots fill a 3 gal container, almost all trees survive and most of them will thrive.
I don't find 1 gal containers any easier or harder to water than 3 gal. They are certainly lighter to move around and dunk, but I don't find 3 gal problematic. When I'm top-watering, I find no difference.