Same situation, but what I usually do is to go to instapaper.com/kindle on my kindle browser to get the last version of my read-later document on my way to work

Same situation, but what I usually do is to go to instapaper.com/kindle on my kindle browser to get the last version of my read-later document on my way to work every morning. No need of USB and I can use it in situations like right before getting into a plane. The kindle browser kind of sucks (now, I am sure they will put more work into that), but I have that URL as the first entry on my bookmarks menu.