Hi,
HikaSerial is design for this kind of work: sell an activation key.
Your key algorithm is based on some information so you need a HikaSerial plugin for the generation.
A HikaSerial generator is like a Joomla plugin (a PHP class which extends from JPlugin) with a "generate" function.
This function is call with several information like the HikaSerial pack object, the HikaShop order, the quantity of serials needed.
It is complicated for a PHP website to retrieve the Windows username but it is easy to get the Joomla Username of to read an HikaShop custom field.
After that, the plugin could generate the serial if you implement the algorithm in PHP. The plugin could call a webservice in order to retrieve the activation key which has been generate by another program. The plugin could generate the serial thanks to an software installed on the software (execute an executable file).
Your are totally free to choose how you want to implement your generator plugin.
I am currently working on different examples of plugins for the next version of HikaSerial.
When an order is confirmed, HikaShop send an email to the customer and HikaSerial could add his serial data into.
The serial is accessible in the website too, in the HikaShop user panel it is possible to show his orders and HikaSerial is integrated in this view too.
About your two last points, it is some HikaShop features.
HikaShop has a lot of payment plugins including Paypal, I am sure that you will found what you want.
The VAT with teh VAT number is supported. It is a feature that we use in our HikaShop store. When you want to buy HikaShop or HikaSerial, you can enter your VAT number and have an invoice without VAT.
Regards,
Jerome