I do 1000 feet over 16 miles on my daily route, and 2000 feet over 30 miles during my Saturday group ride. Although the group ride still has two hills that kill me, these are starting to feel pretty flat. I think 5000 feet would be 'extremely hilly'.
Mon - Fri:
http://www.routeslip.com/routes/13043
Sat:
http://www.routeslip.com/routes/22154