overcoming proprietary software for work

I am a newb and have some questions about running proprietary software
inside Ubuntu or some other distribution.  I have wanted to switch for
years but have three pricing programs that are written for Windows.
My vendors refuse to even entertain questions about Linux.  I am
illiterate about it and would love to visit with someone in person
that may be able to offer some suggestions on how to achieve my goal.
I understand there are emulators like Wine, but don’t want to start
tinkering around and inadvertently let all the smoke out of my work
machine!  Many thanks to anyone that can reply!

Don Murphy
Wichita, Kansas