I use a Big Agnes bag that features a pocket for your pad, beneath you. That added rigidity makes it pretty easy to squirm into the bag in the hammock. I do sometimes use the standup-sitdown method, though, like in Shug's video.
Your sleepingbag has a pocket for your pad? Thats genius why am i just now learning of this technological breakthrough?
Go to Heaven for the climate, Hell for the company.