After several years of using hard SW Motech side cases on my 2012 V-Strom 650 I switched to Nelson Riggs roll top soft bags last year for one reason only. The width of bike with the hard cases mounted (wider than the handlebars) was a major irritant - no threading through long lines of traffic, worrying about clipping something etc.
The result? You're correct, soft bags can be a major irritant when not in motion. Yes, you can put a soft bag inside a soft bag but I found that the inner bag, once fully filled with various irregularly shaped items was often reluctant to squeeze back into the outer bag whereas it would have slid nicely back into the smooth metal interior of a hard case. A struggle would ensue. There are worse things in life but it was a pain.
So, my solution was (using adapters for the racks) to switch to much narrower plastic Givi hard cases. They hold far less that the SW Motechs but you can't have everything.
I enjoyed watching your intrepid Vespa adventures.
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