1. I like Asher as well. Strong, but not harsh.
2. Which meaning is the one you like? When I hear Asher, I think of the Biblical Asher, who was the son of Jacob's slave, Zilpah. Many historians and textual scholars think that his name derives from Asherah, the goddess worshipped by many Middle Eastern peoples before the birth of Judaism. I love that, but I am neither Christian nor Jewish, so using the name of a "pagan" goddess is a plus for me.