Hello, Brett --
Upgrading DotImage only requires a new license if you are switching numeric versions, like from DI 5.0 to 6.0. Upgrading from an alpha version, like from 6.0c to 6.0d, does not require it.
In the installation process, normally your licenses would be left alone -- the folder where licenses reside is not touched. Also, the Toolkit Activation Wizard will run automatically -- you could just press cancel without overwriting your licenses.
(This is just future information, as it seems you are past this point.)
In the cases of laptops, if the MAC address changes, it will look to us as if you are on a different machine.
If you are not up and running right now, I would suggest opening a support case through the portal (http://www.atalasoft.com/support/), so that I can help you with the more personalized information.
Elaine Gorham
Developer Support Supervisor
Atalasoft, Inc.