Open Activity Monitor.app (Applications>Utilities) and check the memory usage, most probably you're running out of RAM (not inside the VM, but globally) when Windows 7 is booting so the system starts paging and that makes some apps hang.
You have a total of 4 GB RAM, Windows 7 is configured by default with 1 GB RAM in PDM, if you are running Safari at the same time, it will very easily consume 1 or 1,5 GB (or more if there is Flash running), Parallels itself consumes about 400 MB, OSX consumes around 800 MB/1 GB also. So it's very easy to exhaust 4 GB, unfortunately. I blame mostly Safari for the memory leakage, but Parallels itself consumes a lot of RAM.
My suggestion, shutdown Safari before starting your Windows 7 VM. you can also try running Windows 7 with less RAM (I wouldn't recommend unless what you do in Windows 7 is very light on resources).
EDIT: The probable reason why Windows 7 starts fine the second time is that the paging has already taken place and there is more free memory to use.
Last edited by a moderator: Oct 6, 2011