I have read the description and fully understand your requirement. The said software can be made by using either of the languages including assembly.
The software would have two interfaces, GUI and CLI, that is, the software can be utilized as a DOS command also.
The software would have GUI in C/C++/VB but have textbased user interface (including tick boxes, radio butttons, command buttons etc) in assembly.
The Windows Preinstallation Environment should not be a problem.
The software will run without installation requirement.
The software will include all the features as described.
In VB this project can be accomplished in 30 days and in C (Modular) or C++ (Object Oriented) it would be accomplished in 60 days and if the coding is to be done in assembly then it would accomplish in 150 days and the price would be 7 times that is $700. I am looking forward for your positive response. Regards.