Draining bilge water

[Road King Cole]

After coming home with the boat on the trailer, I have been removing the drain plug and then jacking the front of the boat up so the water can drain out. I typically crank the trailer jack up all the way, prop up the trailer, crank the jack in, place a cement block under the jack and then crank it up just about all the way to put a sawhorse under it. I found that’s a lot of cranking on the trailer jack.

Is this really necessary except for winter storage? I assume my bilge pump works, but the when its on the trailer the water is probably "midships".

What’s the “easy way”?