First single hand
Yep definitely easier to raise the main first. With the main an that tiller clutch adjusted the boat should sail herself (the main only induces heavy weather helm and the tiller is set to counteract it). Only problem is when the wind dies so does the weather helm which can induce a tack.
On my boat anyway jib only has a touch of lee helm making it unstable for tying off the tiller or handing the tiller to someone inexperienced.
The tiller clutch looks nice. I just have a line tied off to U bolts with adjustable loops that I can fiddle into the right spot.
1979 Contessa 26