hmmm I think it has to be easy since I got it with out even trying. I just relized I had it. I think it was cause I was doing almost every job every day. Some days I was lucky to complete every job in Tir. Its not easy, you have to do some prep work. Gather 20 wool, make sure you got your sythe, have room for armor deliverys... all that. Know what your most likely going to be asked to do.
Sheep Boy always asks for wool.
Healer most of the time asks for wool as well but sometimes does a delivery of pot.
Church is ether 10 wheat, 10 barley, or 15 eggs
Smith is always delivery
Inn is always 10 wood
The 2 that tend to cause the biggest slow down and chance of not completing all jobs is the General Store and Grocery.
General Story alot of times is delivery but will toss in weaving and tailoring.
Grocery tends to be delivery or berry gathering but sometimes tosses in catching fish.
If there is something else that any of these people give you for jobs that I have not listed, its because I never got them. I have done 10 perfect jobs for each of these people (well more for many) and I now I did not have to do that many to get Diligent.
Side note to get Lazy, you have to be doing Sheep Boys quest and then go talk to Duncan about rummors I beleave.
Well hope this helps you.
IGN - Kitiana
A.K.A - Red Head Demon Girl
Server - Mari
Pets - Kitsuna the Brown Fox of Death and Kitamew the Claw of Strife