When I had an AGP, I left a hose in the pool all winter long.
I attached a brick to the end of the hose to keep it submerged. The hose then runs down the side of the pool and out.
But the trick is....have the hose drop to the ground then back up to a shepherds hook (or something to hold the hose up) before it runs out to the drainage area. The reason is, when the siphon is finished and it's sucking air, enough water stays in the raised portion of the hose. When you want to start the siphon again, drop the hose off the shepherds hook, water begins moving (starting the siphon). Remember to put it back on the hook before the water is drained so you can start it again next time.
You can put a big loop in the line when hanging it off the hook.
Another thing I recently bought for siphoning gas is called the Super Siphon. It has a brass ball in the end of it. You shake the end in the water and it moves water up the line - eventually starting the siphon. There is a Pittsburgh company that will sell any size hose. I bought 1/2" for siphoning gas from cans into my vehicles.
You'll want to leave "some" water on the cover for weight, to prevent the cold winds from ruining the cover. If it flaps around, you'll get one good season out of it. If it's not flapping around you'll get two seasons out of it.