Hi Brittany, can you tell me which Little Reader version you have right now -- you'll see the version number in the LR window's title bar or in the Tools > Software Information screen.
About the upgrade for the new version, the upgrade alert is supposed to open your browser directly into your BrillKids Account Management page (it will ask you to sign in if you're not logged in yet). It leads you to the My Purchases > Little Reader Software page, and from there you need to click on the Download button to download the installer for the latest version. It's not going to give you the free trial version, so do go ahead and download the file.
We'd like to know where you found the message that said you're going to get a free trial instead, so if possible, can you please send us a screenshot of this message?
About the error, kindly send us a Diagnostic Report so we can start troubleshooting. You may refer to this article for instructions:
http://support.brillkids.com/entries/20438423-how-to-create-a-diagnostic-report-for-your-brillkids-learning-system