I've had a motorhome (shudder!) and flat hauling with a tow bar is preferable. As low as a Boxster is, it will be a pain to get up on a trailer. I know you want your Box, but I think I'd get rid of it, too. Get something like a 4x4 Jeep or small pickup. Older ones with real 4wd are best, you can shift the transfer case into neutral. If you're running a diesel, you'll have to deal with soot, too. And road debris.
I used to have a Chevy Tracker, it was perfect for towing and it could be set up as a convertible. But finding nice ones that aren't beat down is kinda tough.
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2001 Boxster
2007 Toyota Highlander
2003 New Beetle Convertible, Turbo, Tip 6 speed
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