I tried using a 2 wheel trolley with the 12" SW Dob and it did not work out that well. I ended up constructing a 25mm thick plywood rolling base with locking castors. One of the BAS members has a 14" SW Dob and he moves the scope around with a 4 wheel trolley. It is a two person lift to load and unload his scope. The views at the eyepiece are the reward for the effort.
I have not stored my scope in a shed so can't make any comments about how it would go.
When I had my 12 inch Skywatcher Collapsible dob, I found it quite easy to maneouvre on a stack trolley (Bunnings cheapy). I have attached a photo below....
From memory, the base was around 640mm diameter. I believe the base diameter of the 14 inch is around 780mm. I don't know how easy that would be to move around on a stack trolley. I think the method for the bigger variety would be on a 4 wheel base and pull-handle. Also, with the 14 inch base, I don't think you would be able to get through most doorways.