The largest radius would be 31.85 feet.
We want the area around the cylinder. This is a rectangle whose length is the circumference of the circle and the width is the height.
C = πd = 2πr
The area would then be
A=2πrh
Since each foot of fence is $1, and she can afford $1000, she can get at most 1000 feet of fence;
1000 = 2(3.14)(r)(5)
1000 = 31.4r
Divide both sides by 31.4:
1000/31.4 = 31.4r/31.4
31.85 = r