Long-time Quicken Windows user. Would love to move to Mac version, but at least with the previous version of Quicken for Mac, the basic checkbook register functionality of the Windows version is lacking, IMO, in the Mac version. Specifically, there is full support to move from Quicken for Windows (2010 or greater) or the 2007 version of Quicken for Mac. In my real-world test, with over 70 accounts and over five years of transactions I was able to convert from my Windows data file without issue.

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Depending on the size of file you could even email it to yourself or take it on a USB key if that's a necessary option - but across the network will suffice and is usually the quickest and easiest option unless the file is extremely large (>2GB or so - whenever sneaker net can be faster) Big warning however: Quicken Data files use their Resource Fork to store information. If you use a tool to move the file that does not support resource forks or copy the file to a place that does not keep resource forks around(1). The Finder, and your standard cp, mv, rsync on Mac OS X 10.4 and higher do support resource forks thankfully. 1 - Mac OS X attempts to keep resource forks around by making a separate file with a._ in front of the filename.