Here is the thing with Synced Saves. In most games, save files are around a MB or so in size, and not much changes in the save, other than equipment and way-point coordinates and stats. In Skyrim, the saves can grow to be as large as 15 to 20MB, as everything done in the game creates save data (leaving a door open for instance). With Autosaves being created just about every minute or two, there are so many ways that a Cloud sync would get messed up. I don't know how fast your Internet would upload a 20 MB save file, but it's probably slower than the next Autosave trigger.
The Steam Cloud was used for a while, then it was disabled simply because people were losing progress in the game by getting a mis-synced save. It got to be so bad, that the feature was disabled on the Steam Side for the entire game. I am quite surprised they even brought it back. I would never use it, even if it worked better.
You say that using a USB stick to move saves around sounds kind of complex and cumbersome. Compared to recreating the last several hours of work in the game, it's nothing. Especially once your more recent save gets overwritten by an older cloud save.