I have Outlook 2007, but had this same trouble with previous versions.

The text box give you a huge amt. of space to enter info in the "notes"
section of a contact, but only some of that text prints out on a hard copy if
I have entered more than a few lines of text. I don't even mean full lines
going across the whole text box. Even 5-10 lines of a list or a few extra
addresses or telephone #s can be too much text to show up on a hard copy.
Yet the text box allows for 10 times that much to be entered.

There also doesn't seem to be any rhyme or reason to what prints out & what
doesn't - the cutoff often varies. It doesn't always cut the print off after
a certain # of lines, for example. It appears to be random, though there
must be some reason.

Sometimes, changing around the layout of the text allows it to print more,
but it's not clear why.