You must be earning a lot of miles to track them at the level you describe.

I have used Quicken for about 15 years, at first on a Mac, and then later on Windows. I have an iMac running Windows under Bootcamp, mainly because I need Windows for Quicken (though Quicken 2014 Premier is fairly buggy) and work-related software.

If there was a solidly functional cloud-based financial software package that could import a good amount of my Quicken data, I might switch, but so far, nothing.

Regarding Quicken for tracking miles & points, I'm very skeptical that it would work well. I would suggest a database program like FileMaker Pro or some equivalent.