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I would have no problem with that "cover" - did you make that yourself or is it an aftermarket item?Out of curiosity, why did you part with the Mandello, was it primarily for that reason (wind management) or other considerations?
"One drop was on my ankle breaking it causing lost riding time last summer. "OUCH - sorry to hear that. Hmmm...maybe my original thought that the Mandello is "too heavy" was correct! ;)
The issue is the angle it lays on it's side at. If 20-30 degrees like a Harley you might do it, When I knocked my v85 over in the garage the two wheels were both off the ground as it was completely flopped on it's side. No way in Hell. It took jacking it up from the side to 20 degrees then it still wasn't fun. FYI, no jacks are in the wilderness.