If you transfer 100K or more, you can be assigned someone at Vanguard to do some "hand holding" if you desire. I've done this before and it was a good idea for the first time through the process. That way, as you complete the process, you get to talk to the same person who, in theory, knows what it is you wish to accomplish with all of the gyrations you are going though.
You mentioned "penalties". Are you talking about fund penalties or the befor 59 1/2 penalty? If you've done your homework and have decided that the 1% or so that some funds may charge you for early withdrawal are worth it, I suppose that's not so bad. If you are in the pre 59 1/2 situation, you might seek tax advice to figure your way around that (e.g., 72(t) withdrawals). In any case, don't take penalties lightly. Do some math and get some help to minimize the effects. Just my $.02 worth and Hey! YMMV