Seriously...
It all depends on the situation. The one thing about e-mail and faxes is that you can see the "writing" in advance. And then once all the fine print it reviewed, then any issues and negotiations can be taken care of in person, either face-to-face or over the phone.
However... I don't like contract negotiations at all. Talking money has never been comfortable for me. Thankfully, with most union gigs, the scale/pay is already pre-determined by the union and the theatre/producer. I don't have to negotiate anything - just pick up my check each Thurdsay.
In the cases where I've had to negotiate, I always prefer for "them" to give me a figure first rather than having them ask me for what I want. I usually end up under-selling myself - at least that's what I've been told. Heck, as long as it's over minimum wage...
I also get very uncomfortable when I'm dealing with actors who aren't yet established - i.e. they have day jobs. Some people have seemed shocked that my rates are so reasonable. My general rule of thumb is: If I know you can afford "it", then I will bill you accordingly. Otherwise, I'm there to help you further your career not to empty your bank account.
And then there's the ultimate uncomfortable situation... Talking money with your parents.
