Personally I LOVE the Mac. My wife and I bought our MacBook earlier this year so that she'd have reliable laptop for her college work. I "tinker" with music and video editing, so naturally I enjoy Garage Band and iMovie, etc.
However, I should have done my research. I'm even in IT field, so I feel pretty embarrassed to admit this. There are several websites that she has to use for her both her college work and her day job work that will only work with Internet Explorer. She had issues with some of the functionality on the FAFSA (Student Loans) website with both Firefox and Safari, problems with some of the test taking software for one of her online classes and was unable to view her online pay stub on the website of her employer. In her words the MacBook has been "one very expensive facebook browser".
And yes, to answer your question, I did try Winebottler.

I've done research on some other solutions, but to no avail. Any suggestions though would be greatly appreciated.
I knew that 10 years ago there were websites that were IE specific, but had no idea that those are still around...This has caused me a lot of grief. I just wanted something with a more reliable OS than Windows so that she wouldn't encounter issues while doing her homework.