Yep. It was Dave Cornthwaite who started it all for most us at the time. Nice guy.
I did most of Jogle myself in 2009, but ended up in hospital after a crash on dartmoor less than 100 miles from the finish!
The bath to Bristol was the classic, I did the first few with the Skatefurther lot.
Yep, I pushed both sides (you get good quick and the trailer aids stability). I found that you kind of changed your pushing style to save the pummelling effect of hitting the floor. You tend to lean forward more and pick up the ground on the way through. Very low deck height too, so less far to squat each time. I was 'working' with subsonic skateboards at the time to help with the design of what is now there GT40, I had the prototype for most of my trips.
In turns of boredom, once you get fit, you go pretty quick. We went out for a 40 miles skate on my stag do in 2016 and the best man's brother couldn't really keep up on a bike. (It had been a while and hips were fucked afterwards).
It was the distance skating that eventually got me into cycling. I just liked the endurance side of things.