I have tried placing a big block under my trailer jack and raising it all the way up, high enough that the front wheels on the trailer are off the ground, and I can't ever get it high enough to drain. 

All my bilges are working correctly, and when I pull the boat out of the water there is very little water in the bilge to drain.

There is a slight hill coming out of the marina driveway, so I will pause there and that gets the bow up enough to get a little more out, but not all.

Is this just how it is or is there a trick to getting that water out of there?

I am on standby for some tricks too?

Here's a picture of a 97 sport open bow from the internet.

I guess if yours is like that, I'd pull the cushions and find a spot for a small hole to be drilled above the deepest part of the V where the water collects, so I could suck out the water.........or take 63 Skiers approach but it sounds like you want to get it out of there.

I'd figure you could put a removable plug in the hole or just leave it open for more drainage from up front. 

I think I will try waiting longer on the hill in the marina parking lot to see if I can get all out of there. 

Ken, my '98 was first year for the non-slant-back Sport/Air, but I'm guessing same bow configuration. Below the front 2 bow cushions is a hinged removable filler, with that out its open to the carpeted storage space below. I pull that and lift the observer seat to let it dry out after being on the water. But at the bottom right at the bow there is a metal drain so there has to be a chamber below where the water collects.

Mine is a SS/Air Natique 99 the cushions are slightly different. I never noticed the problem you speak of until not taking my boat cover to the lake camping. Then the Dixie fire in California 2021 started, smoke and ash for a few days and I thought the fire crews may get a handle on things so I stayed a few days in the smoke. As I realized the fire was getting worse I pulled the boat out of the water and it was full of ash and soot.Then pulled the Airstream trailer home also.

Once home after vacuuming out the boat I washed it including removing the cushions and spraying lots of water. I had the bow jacked way up letting what I thought was all of the water drain out. I was going to let the boat sit out in the sun for a day or two to dry out with cushions removed and then the ash from the fire reached my home. So the boat went in the garage. About five days later I went to install the cushions and I smelt a mold smell, my ski locker had a small amount of water still in it and the very front compartment/battery compartment still had wet carpet.

So you are not the only one with this issue it is a design issue. My boat is still in the garage as I still have ash falling. I live in the mountains so no matter which direction I am towing I have large mountains to climb so on  the occasion the bow gets water in it, it usually drains out out of the bow prior to getting home and has never shown up prior. I always pull the bow cushions when I get home, place the battery on a trickle charger, and open all compartments and hang up wet vests and such.

On mine you may be able to vacuum out a little water from the carper around the drain but it would be very little. The water on mine drained to the ski locker as that is the low point when sitting level. At that point I could vacuum or sponge it out. I think in most cases the sun would be your best friend with cushions removed and compartments open but that is not always an option.

So, what am I missing here?

You pick a spot, drill a hole, stick a tube down and suck out the water, or get what you can and leave it..

Must be an aversion to holes