getting activesync to work flawless is hard enough ... I dónt think you should expect your PC to boot up loading other programs and along with that connect through activesync all in one operation ... think of the loading and operations behind the scene... and
the order of process when starting up a PC is not always the same .. if you take a look at the corner beside the clock during a startup ... you will noticed that things are not always start in order ... they might all start ... but not in order everytime ... and this will contribute to your problem.
I think the majority of us users go through the route of having the desktop already running and then dock the device as a second step operation and some are crossing their fingers for successful AS connection ...
hope you understand what I am trying to say !