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#11
If you Reset, you get back to where you were with the initial Windows 10 Upgrade - no programs installed, no personal settings. The 'Keep My Files' option only keeps your User files intact, like Music, Pictures, etc NOT programs. The idea is give you a fresh copy of 10 incl updates since your initial upgrade w/o having to reload your personal files but you DO have to reinstall your programs. Sorry for the bad news but you're no worse off than having to rollback and upgrade all over and it's quicker.
Making you reinstall all programs is not so bad because, if a program was causing your problems, you get to start over. In your case, this would be the ideal time to reinstall Quicken and run the exe after a compatibility check. Good Luck.