Not on trailer straight.
I’ve read a lot of blogs on how fellows load their boats and many of these procedures are far more damaging to the hulls than maybe your situation. Guys who do not want to get their tires wet and winch the boat up out of the water like a power boater or have to slam on the brakes in the parking lot to slide the boat forward on the bunks to name a few.
You will have to do your own evaluation on how crooked your boat can be without causing damage. With a swing keel the bunks carry the load of the hull and the keel is let down on a trailer cross member after the boat is recovered and out of the water but, a wing keel sitting on this cross member at such an angle that it lifts the hull off one of the bunks can cause problems.
Look at the bottom of your wing keel, is it sitting nice and flat on it’s own bunk or cross member?
Now look at the hull bunks, does the hull seem to fit the curves of the bunks?
Take a thin plastic ruler, can you slide it down between the hull and bunk many places as compared to the other side?
Placing a boat on a trailer without guides is a real pain!
Powerboat's have nice straight sides that allows easy placement of hull guides on the trailer but, the shape of sailboat hulls and keels really creates many problems on guide placement, one has to be very creative.