Lift the bow and trolley up in the air until the transom hits the floor. Then rest the transom on something soft (a lawn, a blanket, some fenders, etc.) Have your wife pull the trolley forward while you push the bow up. Do it in three steps. In between steps rest the boat on the trolley while you step over the supports or the axle.
The procedure to get the boat back on is the same but in reverse order. The trick is to move the trolley, not the boat and use the leverage given by the trolleys roller once the roller passes the middle of the boat. It can be done by one strong person and his wife but lifting the bow by two persons is much easier. The person moving the trolley does not have to be strong.
The hardest part is when the boat is already resting on the trolley and there is one more foot to go to slide it in to the rubber bow rest. This needs a good strong pull with someone blocking the trolley from moving forward. I do this by putting a part of a railway sleeper in front of the jockey wheel and putting my foot against the sleeper while I pull. The (partial) railway sleeper is otherwise used to put the jokey wheel on to put the boat level and allow it to fully drain through the self bailers while it is parked.
I have seen a road base with a winch on its draw bar to pull the trolley on. Maybe such a winch can also be used too to get the boat back on, provided the trolley is mounted to the road base?
The American way
Another method is to tie the boat to a tree and pull the trolley with a car (rope – tow-hook). Here too the transom needs to rest on something soft before you start pulling. Again this is done easiest by pushing the bow up. In this case you don’t need to lift the boat of the roller but you can let it slide over it while a car pulls the trolley. Good communication with the driver is paramount because the bow pushers will have to step over supports and the axle. This is why I prefer the manual method, it has less chance of someone ending up in hospital.
To get the boat back on you could pull it with a car while the trolley is tied to a tree but this has the big disadvantage that the boat moves and not the trolley giving a greater chance on hull damage. Maybe if you can tie the bow to a tree and pull the trolley in reverse under the boat?
What ever you do don’t use piled up stuff to support the boat more or less horizontal. These piles trend to topple over once the weight of the boat rests on them. Just put it directly on a lawn without a circus act.