That being said, after a few updates, Quicken 2015 seemed a bit more stable than prior versions. Intuit never seems to correct fundamental bugs in the program as they do not have to and their India based telephone support is not always able to solve problems. However one tends to make errors entering numbers into spreadsheets that are less likely to be seen in data downloaded directly from your bank into Quicken (my accountant proved this to me). There are many alternative ways to do basic book-keeping, particularly customizing your own spread sheet. Better research tools are available for free online from many sources than are built into Quicken. I do not know of any other program, iffy as Quicken can be, that can replace it for most individual investors unless you can program your own data base. Windows is not like OSX, it has backward compatibility to almost but not quite anything written for it in 16 bit code (emulators can run DOS). If that is not important to you, and why would you use Quicken otherwise, then it does not matter what version you use with Windows 7-10. I upgrade Quicken every two to three years because they threaten to cut off automatic updating of stock prices if you do not upgrade. That is not why most people turned to Quicken and MS Money in the first place. Both will limit in the extreme, both your investment and financial options, and make all but the most basic convenience features a thing of the past. The only alternatives I can see is to keep your records on paper with a complex manual filing and retrieval system or with an electronic spreadsheet that never attempts to connect to the greater world. I'm not saying your concerns are meaningless or misguided, far from it, but I am saying that you might be looking at one specific tree, while you are ignoring the other trees in the forest that have every bit as much effect on your financial health. If you enter your Fidelity account information on your bank's financial planning page, or on your broker's planning page, you have made a similar security compromise. if you access your financial accounts online for informational and planning purposes, you have made a security compromise.
If you pay bills online, you have made a compromise with security.
That bothered me at first as well, but then I realized that all my information is ALREADY out there and collated by others.
This is one area where I shy away from cloud offerings, as it seems like they benefit more from the arrangement than I do. Using quicken required data entry, or giving it lots of account info, but you could secure it as much as you felt necessary, unlike the online offerings that all want to collate your information.
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