Frustrating. I've only restrung mine once so far and I broke the high E string the first time so was glad I had two sets of strings. The windings on the pegs didn't turn out all that pretty either, but I don't have to adjust the tuning constantly so it's good enough, just not very pretty. Hopefully I will do a better job of it next time.
It takes as long as it takes unless you quit - then it takes forever and you will never get there.