Enclosed trailer question (thinking of upgrading)

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Hi everyone,

Had a blast at the 60th anniversary event (pic attached :-D). I'm thinking of upgrading from an open trailer to an enclosed setup but I have a few questions.

For context, I am towing with a 3/4 ton diesel Silverado and I am currently planning to tow around a Miata and a Porsche 996 Turbo. Currently I don't have a gooseneck however I wouldn't mind installing one if it would make sense to do so. Also, I have a fairly tight driveway so as much as I think it would be cool, I cannot get away with a monster sized trailer.

Onto the questions:
- What size trailer makes sense? To me it seems like a 20' trailer is the minimum however a 24' seems like a popular option that I have seen. I'm thinking the 24' trailer may be too long for my driveway unless I can go with a gooseneck option.
- At the tracks for the DE events, can I leave the trailer for the weekend while competing?

Thanks!