Weather is crucial.
People paddle and row the channel but they do it when the weather is good, with a predictable weather pattern, and some times of year are more predictable then others.
I'll be honest Sept October is iffy.
I fish for Billfish Off Avalon in a small skiff that time of year and weather wise it's not a very predictable time of year. Almost every day starts out flat then around noon wind comes up from west. Some days it's 5-10 knots of wind some days it comes up 20to 40 knots rips down the channel and generates 10ft confused seas.
Several times on days where there was supposed to be just mild conditions I've seen winds come out of nowhere. Sometimes it happens so fast so quickly that you actually see the whitewater before you feel the wind.
There have been times I just barely made it back to the shelter of the island and another time I tried to beat the wind back and ended up fighting the wind half the night and barely made it back to shore.
I kid you not the worst conditions I have ever been in on my skiff anywhere ever, happened right in the exact area you want to cross, during that time of year, on a day they forecasted little or no wind.
I could of died, I know of other people who have died in similar wind events in small boats under 20 feet.
This is a known weather pattern and I've got stuck at the island for days because of it.
Actually I researched this before and I think the best time of year to paddle across is coming up shortly, flat calm late winter conditions are the most predictable. The guys who do it also start out in the middle of the night so that they can be across before noon.
You may think this is easy or safe but if you get caught in a fall wind event in that channel in the kind of kayak that you guys fish your going to be in big trouble even if you have a support boat.
Just saying, Jim