From maintaining the system and working with it, you'll probably already know the areas of the system which tend to be buggiest, which tend to change often and which tend not to change very much. If you don't, you can always look through the source control logs (you are using source control, right?) to find out where most of the bug fixes and changes are concentrated. Focus your testing efforts on these classes and methods. There's a general rule called the 80/20 rule which is applicable to a whole range of things, this being one of them.