I may be pressing the wine this weekend (would like as much time as I can muster on the skins, so I might hold off until Monday or Tuesday of next week). If I punch the grapes one last time on Sunday, wait for it to form a good, solid cap and poke my racking cane through the cap, I can pretty much vacuum out most of the juice, yes? Once the juice is out, I can more easily haul the brute out to the garage to press the grape skins to get the remaining juice.
Theoretically, yes, but mine still has a tendency to clog, making for a slow racking. I use, as others, a tube with holes in it that gets pushed into the must and siphon out of that, it helps.