A:AnswerNo - numbers go into the same directory that is accessed by all phones. So you only have to enter numbers into the directory on one of the phones and all others will see it.
A:AnswerI do not see an option for any head set when looking at the phone but it may be possible to set the portables phone on speaker phone and set it close to where you may be working.
A:AnswerI purchased my own set including the additional 3 handsets. However, I purchased a new set for a friend and also at Best Buys, purchased a couple of additional handsets for their set. They did not have a problem adding them to the base. You need to look at the manual for directions on how to make them connect.
A:AnswerI have seen the headset for the two-line phone. I decided not to buy it because of the cost which, because it's a 2 line phone, is much higher priced than typical headsets for single-line phones. It's available, however.