Lead Balloon, we're not sitting in your aircraft so have absolutely now way of knowing what the view is like through your windscreen. You're flying an aircraft so the assumption is you're competent to do so & will advise if you're unable to comply with an instruction or need assistance. The pilot was in VMC when he initially requested clearance & would have remained so if he'd continued deviating right as he initially started doing. It would have added very little to his workload, no more than a deviation around a region of cloud would have.
The basis of your experience of a single flight with an ATC? Maybe, just maybe he applied a great deal of local knowledge to achieve the flight? Something a local operator would have as much knowledge of.