For your first question:  You might want to take a look at some free Word
templates that use your Outlook calendar data to create a calendar in Word,
which you can then customize to your liking.  I personally use My Outlook
Calendar and am very pleased with it.  Links to these templates can be found
here:

http://www.slipstick.com/addins/calendar.htm#print

For your second question:  If you have put the business and personal
contacts into separate categories, you can create a custom view that filters
out one or the other, and then print the view that shows only what you want
to print.