During a period of unemployment from a "proper job", I once became a paid professional winch driver for a gliding club located on top of a Cotswold near Stroud. Suffice it to say that that job was (strangely) considered untouchable by many of more affluent club members.
Driving the winch eventually becomes an art - controlling the aircraft's speed by assessment of the bow in the cable, and flying him in the last stages of the launch like a kite.
Make a point of flying from as many sites as you can. You will become so aware of weather and topographic effects, sea-breeze fronts, ridge curl-over...
It is very time consuming but very rewarding.