To answer your questions:
1) The software that came with the board might be an Evaluation or a Special Edition version. A Special Edition version will be fully functional, except it will have certain limits or restrictions. An Evaluation Edition is fully functional, except its license key will expire over a certain interval. Then it behaves like the Special Edition. The other issue it that the tools that came with the board might be a version or two behind what's on the site. You can download the latest version of the Special Edition and experiment.
2) Special Edition software will let you do enough to work on small project to give you an idea if you want to use the tools. Ideally, you'll like them and upgrade to a Standard Edition, 
but the choice is yours.
3) I don't know what the expiration date might be, it varies. However, if you do a build and see a message about the license has expired in the Warnings and Errors window, then its obvious the license has timed out. However, an expired license shouldn't disable the debugger interface.
The parallel port interface can be fincky at times. Adding a peripheral can drag down a laptop's power level such that the parallel signals become unreliable. However, that would cause flaky operation, and not the connection error message that you're getting. I'd start with checking the debugger settings to see that the parallel iterface is selected and check what printer port it is trying to use. Confirm that this printer port is the default one and active in the system software. These things just don't stop working. Something has changed.
---Tom
