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Hey Ben,
I've had my Skywatcher 8" Dob for a year now and wrestled with the same problems to begin with.
I tried the trolley (Bunnings have one for $25) + strap route which worked a treat but you need to be careful not to knock the collimation out setting it down.
Honestly I got fed up strapping it onto and off-of the trolley and unconsciously reverted to the crab shuffle carrying the whole thing by the tensioning handles. Less faff = more motivation.
Enjoy!
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