I am trying to improve my "system" to prep the boat and get it to the water as quick and easy as possible. My driveway has a decent pitch down toward the road. In order to get the trailer tongue high enough that the boat drains out the back I need to raise the tongue 40 plus inches. I already have the highest lift tongue jack I could find (about 35 inches). Currently I need to drop the trailer into a stand, adjust the jack foot, relift off the stand and drop to the hitch, and then opposite to unhitch.

What do you do? Any tips to streamline the process?

2 jacks, one on each side on the frame just in front of the fenders a foot or 2

Are you storing boat outside or just pulling the drain plugs after a day of boating? If the latter, I try to pull the plugs on the ramp (as long as people aren't waiting on us) - although I get very little water in the bilge, unless we got rained on.

The boat stays outside.

Good tips guys keep them coming

2 houses back, my house was on a rise on the lot. Backed into the yard for parking required large solid concrete blocks under the tongue jack to keep the nose up. I had two tongue jacks on the trailer, and use the 'step up' method, where I would raise it as far as I could with one jack, and then lower the other one onto the block, and raise it high as I could.

Sometimes, if I knew I was going out a couple days later...
...I would pull into my driveway, and pull the truck into the garage stopping so the coupler of the trailer was just outside of the garage door. Then drop the trailer, and pull the truck into the garage so I could shut the door. Unfortunately, this put my drives and props right at the street and vulnerable to theft, but I never had any issues. But it was an option that worked really well and used the slope of the driveway to my advantage.

Pull in your driveway truck first, so back of the boat points down.

BTW/: never run your boat on the trailer if your boat is azz high. Seen a few people hydrolock their motor this way.

Think the two jack idea is just what I was looking for. Thanks for the tips!