Switching from Windows Mail to either Mac Mail.app or Mac Outlook (help!)

Hello,
My wife has been using Windows since forever but I'll be getting her a new Mac next week. I've been using Macs since the Mac Plus so I'm comfortable with her making the switch. The one main question I have is about her email.
I registered a domain for her a number of years ago (she uses POP3) and she uses that domain for her email. She currently uses the basic Windows Mail application (not Outlook). She has a large number of emails filed away into a ton of nested folders in Windows Mail.
I'm debating if I should have her use the Mac's Mail app or if I should but Outlook for Mac for her (part of the Mac Office suite). A few questions:
If I have her use the Mac's Mail app, is there a way for me to export all of her contacts and emails from Windows Mail (including the way all of her emails are organized into folders) and then import those into the Mac's Mail app? (and Contacts)
Does the Mac's Mail app support a lot of folders, nested multiple levels deep? The last time I checked (a number of years ago) it seemed like nested folders to organize downloaded emails was an afterthought at that time.
Any idea how I would go about exporting saved emails and contacts from Windows Mail and import them into either Mac Mail or Mac Outlook?
Thanks!

Mail allows for nested folders and complex rules for automatically filing items into these folders as they're downloaded to your local computer.
Any switch in technology can be a little daunting and annoying at times, before you try transferring a lot of sensitive information let her use Mail.app for a week or so and get to know her way around and feel comfortable with the features, then make a decision on how to import old information.
Outlook for mac is a large complex and expensive piece of software, there are other mail options available in the App store if Mail doesn't cut it.
If she wants to try the new program and you don't want to disrupt your POP3 settings on that domain, try a google account.
I'm not sure how Outlook is made available, but there are many Windows emulation programs if she cannot leave some programs behind.

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