trailer insurance in MD is cheap, I was quoted >$100/yr for a fully enclosed trailer and less than half that for something like a harbor freight trailer, tags would cost more
that said, I think the harbor freight option is the way to go here for you. I'm looking into enclosed trailers but I also intend to go hardcore into track days (eventually racing, years down the line) and get a lot of use out of it so the extra money makes sense
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