At various above…
Should be able to find and pull the skirt loop with one hand. The other is likely to be busy hanging onto a paddle. IMO any skirt that you cannot pull off with one hand even with tired due to tightness should not be worn.
I choose skirts that are leakier than some like. But they will come off if I am not at the top of my game, which is when shit often happens.
On air and water temps and rolling etc
Paddling in Maine, a normal situation all summer is hot summer temps with water in the 50’s to low 60’s. So for those of us who are not locals, who generally do better at acclimating to the chilly water, we are paddling in dry suits or neoprene for the water that are downright hot for the air on a sunny day. To avoid overheating it is necessary to do rolls, sculls, balance braces in fairly chilly water.
As above there are ways to get down in the water short of a roll. But as raisins said, most are best executed if a roll is in the tank in case something slips. Especially if paddling solo. The best way to cool off in warm weather is to get your body in the water, but that involves a skirt.
This is why rolling should come as early as possible, at the same time as learning stuff like paddle float reentries. Especially if solo paddler. Balance braces are a lovely way to cool off, and as above do not require securing stuff like a roll. Have to admit that it does come easier for smaller people and females than for many men. The combination of the flexibility required and where the weight is.
Waiting to start a roll becomes a self-inflicted problem. If it is learned or approached as other than a natural continuum to sculling/braces other deeper water skills, it becomes a “thing” that is bigger than it actually is.
Greenland training gets this right, most other approaches to sea kayaking have a disconnect there. A roll is just sculling up in a single stroke. With a properly fitting boat the complicating factors are what humans add like bringing the head up to early (my bete noir) or not using the lower body well. But that is still all it is. Even when it was taking me nearly two years to get it, because of some issues with claustrophobia once I had to stay in the boat upside down, I knew that was all it is. The roll was not the problem, my anxiety was.
Disclaimer here, have to admit that with the various disruptions of this season my roll even on my right is vague at best. For the first time in well over a decade. So when I paddle in Maine I am relying a lot of being very conservative about conditions and being in the Romany, which is a very kind boat to various alternate forms of self-rescue.
But I know that it is in there with some serious time on sculling, as well as the left with more time, and that will be remedied before I try paddling either a more challenging boat or in more challenging conditions.