My vote is also for DeLaval style bucket milker for two plus cows. At the risk of sounding like I have some vested interest in the company, (I don't) I would recommend looking up BobWhite Systems in Randolph Vt. or Parts Dept in Sharon Ct. The BobWhite Systems folks are really good at just this kind of setup and have a milking system package price for a small setup dairy that I think is a fair price especially because they are always happy to help out. Whatever works for your setup is what is best for you, I'd only suggest steering clear of a belly milker.
This book is intended as an inspirational manual for keeping a family milk cow. A lifetime of practical experience has been bound into one volume. Practical advice for the everyday and procedures for cow emergencies. Plus, answers to FAQ's like, 'Should you get a cow?' and 'How Much Space do I need?'