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This is what I might try and I have been doing the same on a 3 year old gelding I have. First I would ensure the horses can back up off a soft feel. He should stand still with a loose lead rope on a halter, and when you pickup the lead rope and wiggle/shake it, with as minimal energy as you can get by with, to get him to back up. What I work for is soon having him back up when I just pick the loose lead up and hold it head high. That shows he is operating on a soft feel. You don't want to have to chase him back. That's going to work against you when you are asking him to back out of a trailer when he is already fearful about stepping out into space.
Another thing I find useful is to back him along side a fence. I start first by sending him along a fence, and when he is good at that, I narrow the space between myself and the fence and send him. You only do this if you feel he is sufficiently good enough about going between you and the gate - you don't want your horse to run you over or step on your feet. Soon I'll stop them right between me and the fence, and I'll ask the horse to back a few steps. This also works as preparation to go through a gate, especially narrow gates.
Once the horse can back softly on firm ground, then you might try leading him onto a piece of plywood or some other platform that is close to the ground and when the horse does that willingly and softly, then stop him on that platform and ask him to back off it. I actually don't use plywood, but that would be a good low platform to start with. I have a bridge that I sometimes used in the Arena Challenges that I put on in the past, and the bridge is narrow enough to neceesiate having your horse backing straight so he doesn't step off the side. It's also a good exercise for you and the horse as you have to be accurate with your timing when you ask him to stop in the middle of the bridge after he steps on.
I use my shoeing stand which is on the back side of one of my hay barns and has three open sides. My 3 year old is comfortable here as he has been trimmed a half dozen times or so on the shoeing stand. I start with bringing him onto the shoeing stand from the lowest side, maybe a four inch rise from the ground. Get him settled then ask him to back off it and give him a pause. I actually let grass grow on this side, fed by the water run off when I hose down the stand. I let the horse take a few bites of grass. Then I'll move him to another side of the shoeing stand that is maybe 6-7 inches off the ground and ask him to step up.
I'll repeat getting him settled then ask him to back off the stand. I do this as many times as he needs to step confidently and without worry. Then I move to the highest side of the shoeing stand which is about ten inches off the ground and repeat the whole process. The video below is asking my three year old Curly Zeke to step off the high side of the shoeing stand.
When you get him back into the trailer, then you may try this: Bring him as far into the trailer as you can. Then ask him to back a step or two, stand for 5-10 seconds, bring him forward and repeat. As he gets more comfortable backing a few steps, you can ask for more steps, but as the trailer flooring feels much less stable than the ground or rubber mats on a concrete shoeing stand, the horse is going to be a bit less confident about backing and stepping off into space, so give him time to get comfortable.
And finally I think there is no bad stigma on turning a horse around in a trailer and leading him out,......in the beginning. Every time he is led into a trailer and is comfortable, he gains confidence, and soon the less than absolute stable trailer floor concerns him less and less. But certainly before you turn a horse around and lead him out, try bringing him into the trailer as far as you can and giving you a few steps backing. I would try all this a few days in a row and would be very surprised if he wasn't backing out of the trailer in an increasingly soft manner by then.
