Hello
I would do it with Powershell.
Every task will be a separated *.ps1 script file written in Powershell. It is good, because Powershell is integrated in Windows and later we can expand the tasklist easyer.
There will be a main *.ps1 file, which will invite and start all the scripts in the proper order.
You can place the script files and also install files(skydrive, adobe..) on a network shaer, not need to copy every machine. When the user logon, the script will automaticli run a fast check, if something missing or not properli set it will take action.