[Mark McLeod]

I wouldn't put the sequence you describe into Teleop.
It'd be easier on you to put a sequence like you describe into Periodic Tasks.

So, your sequence can be thought of as these discrete frames:

1. Retract solenoid; Wait 500ms (half a second to give the retraction time to complete)
2. Set Winch motor to speed (1.0); Wait 3000ms (or however long it takes the winch to do it's work)
3. Set Winch Motor to 0 speed
4. When does the solenoid get extended to complete the cycle?

Here's an example of something similar: