First, I wouldn't uninstall anything until you get your programs working satisfactorily under CrossOver (unless you're very tight on disk space).
Second, you don't want or need to install Windows XP with CrossOver. CrossOver is for running Windows programs without needing the Windows OS.
Third, yes, you will have to reinstall Quicken into CrossOver's environment. It can't use the version installed into your Windows disk image because it won't have access to the necessary registry settings. Doing that is something that we've investigated from a technical perspective, and it is theoretically possible, but so fraught with problems that we have suspended work on that feature.
Please Note: This Forum is for non-application specific questions relating to installation/configuration of CrossOver. All application-specific posts to this Forum will be moved to their appropriate Compatibility Center Forum.
CrossOver Forums: the place to discuss running Windows applications on Mac and Linux
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