This question is difficult to answer as it depends on the size and complexity of your project(s). The "big" releases (from 1.1 -> 1.2, 1.2 -> 1.3, 1.3 -> 2.0) usually break stuff and so you have to budget some migration work. The migration between "smaller" releases (for example from 1.3.9 to 1.3.10), on the other hand, is usually easy, often it just means to replace the cake folder. In both cases it is useful to have tests.
I migrate the projects which are actively maintained.
You can find the CakePHP version in cake/config/config.php