Normally it’s not lack of Windows compatibility breaking the use of an application with wine, it’s the frameworks and libraries the application was built with/need to have access to.
So check what additional libraries and stuff your application have as a prerequisite. Visual C 2005? 2010? DotNet framework? Which version? And so on.
When you know what the application needs, then you can Google for “wine DotNet 4.5” (just an example) to get a feeling what problems people had and how they solved it.
Essentially wine needs to know where to find them when you start your application with/in wine.
Also, if your application uses MSSQL Express or similar, you might be out of luck. So if that’s the case you should start googling on how to get that running (if even possible) before installing.
Good luck, be stubborn and make sure to have fun. There’s a lot you’ll learn in this adventure of yours that will come in handy again and again in the future.
To be honest, it was ages ago I started up wine so I’m the wrong person to ask.
I’m a dual booter, best of two worlds, full support from vendors and no compatibility problems is my preferred way