Reasoning
If we denote Alex by A, Billie by B, Charlie by C, and Drew by D and number the clues.
If Alex had three more sheep, then he'd have one fewer sheep than Billie.Whereas Drew has the same number as the other three shepherds put together.If Charlie had three fewer sheep, he'd have exactly three times the number of Alex.If they were evenly distributed, they'd each have eleven sheep.
By (4): A + B + C + D = 44
And, by (2), these are shared equally between A + B + C and D.
Answer
Here are the contents of the containers after each stage:
A B
0 11 fill B
7 4 fill A from B
0 4 empty A
4 0 fill A from B
4 11 fill B
7 8 fill A from B
0 8 empty A
7 1 fill A from B
0 1 empty A
1 0 fill A from B
1 11 fill B
7 5 fill A from B
0 5 empty A
5 0 fill A from B
5 11 fill B
7 9 fill A from B
0 9 empty A