I believe this may be a niche question but hopefully someone may have an answer.
Has anyone gotten PipeMax working on Linux? Or does anyone know of a Linux native alternative software for automotive engine design? I'd rather not purchase a software for $100 only to not be able to get it working. I am not very knowledgeable on how to get Windows programs working on Linux as I've tried using Bottles and Lutris for Zwift but was unable to get it working.
If you're not tech savvy enough to get the software running under for example Wine, you might be better off with Windows.
Trying to get support from the vendor for anything not Windows will not be easy if even possible.
Anyways, If you're still going for Linux, I guess that Wine is what you're looking for.
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.