Winter project, tow out gear - wing wheel

I have to refurbish/replace my wing wheel assembly and need some
suggestions/insights. The current one is the typical aluminum wing
cuff and bicycle wheel. It wasn't well made to start with and it's
falling apart. I want to take this opportunity to improve the thing.

One of the biggest issues I see is that if the cuff isn't perfectly
aligned on the wing, the wheel will try to track sideways and cock the
cuff risking wing damage. Further, it's a big chunk of "stuff" that
takes up space in the trailer or retrieve vehicle.

My first thought is that there are already wing cuffs used as wing
supports in the trailer. One of these might serve a second purpose as
a wing cuff for the tow out gear if I made it a little wider and added
attach points for a wheel. This would eliminate the need to find
extra space for it.

My second thought is to use a castering wheel instead of a fixed one.
This would prevent lateral and twisting forces from being transferred
to the wing. Even if the wing cuff wasn't perfectly aligned, it
wouldn't matter. The wheel/fork/steering head from a child's bicycle
might be adapted. I'm thinking that the typical ~20" wheel is much
larger than it needs to be.

Further thoughts about wheels leads me to think a bicycle tire is
designed for traction which isn't really needed in a wing wheel. In
fact, it would probably be better if it would slide sideways more
easily than a rubber tire. Pneumatic tires also can go flat. Maybe a
solid plastic wheel from some other source would be better.

Any thoughts?