FWIW I find that it is much easier to load and transport my Hobies (Adventure and Oasis) right side up in cradles.
I always transport them stern first so that the rudders don't need to be bungeed. Having the boats the right way up means you can leave the seats on the boats and the seat backs will lie flat in the slipstream, and you can then load them up with gear through the various hatches: I put my fishing gear, paddles, masts, sails, clothing, PFDs, etc inside them; the daggerboards go inside a boat or in the luggage area and I put the cart on top of them and bungee it down (though nothing seems to want to fly out of the luggage area when travelling even without the bungee). I don't even take my fishfinder off the boats unless I am going to stop for a while somewhere - usually I just lie it down below the gunwales so that a casual looker would not even know it was there (but then this is New Zealand!).
Pretty much all need to carry inside the car is the people and the drives.
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