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Novice : containerize software

Hello community,

I am new to using docker and would like some feasibility advice on the idea I have.
It is a software developed in C ++ that I use daily for my work.
The problem is that there are several versions of this software linked to the version of windows.
This software works with a database (ms sql).
My wish would be to be able to containerize the server part and virtualize the client part (like with the software cameyo).
In use, I would like to be able to launch a database version and a version of my software on the server side with Docker and on the other use a usb key with all the clients encapsulating with an application virtualizer.

Can you help me, is it achievable?

Best regard