What's the best way to break my rig while towing?

I think I would be seriously thinking about the trailer idea... how big of a trailer are you thinking? It won't take much of a trailer to haul about 350lbs.
I don't really know the tongue weight on smaller enclosed trailers, but I have a smaller two wheel golf cart Ziemann trailer that the tongue weight is pretty minimal. I would drag that along if I were in your situation.
Just an idea