I resolved my scaling issues with Quicken 2014 by checking 'Disable display scaling on high DPI settings' in Windows on the Quicken shortcut (see attached screen shot).
I'm running a Mac 5k 27" with Parallels 11 and Windows 10 -- I was having the Quicken 2014 resolution issues mentioned, too.
I have my Mac's Display setting set to 'Scaled' and set to the far right 'More Space' option.
I have my Windows resolution set to 2967 x 1668 with scaling at "100%".
I have my Parallels Graphics > Retina Resolution set to 'Scaled'.
Given all the above, Quicken 2014 now shows up as expected in Windows (all fonts are scaled the same and everything is readable).
Not too obvious and I didn't see this mentioned anywhere else. Good luck!
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Side note: To get to the Properties page attached here in Windows 10, search on "Quicken" in the Windows search bar, right+click and select 'Open File Location', then right+click again and select Properties on the Quicken 2014 shortcut, then select the Compatibility tab.
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Last edited: Nov 25, 2015