Wine is not hard to you use, what progams are you trying to run? Usually there is a Linux app that is just as good if not better.
If you are curious about your windows program working go to google.com and type in the program name and Wine HQ and there will be a site for wine HQ that will pop up and tell you if it works or not. You can get wine from the website or your Ubuntu software manager.
If you do find Wine to hard to use the download a program call Play on Linux and you will find that way easier since it has a graphical interface.
As always I recommend to many Linux users to search for a Linux program that is open source cause in most cases there is a version out there. It is better to use something designed for your OS plus it supports the open source community.