[573v14n7]

Microsoft Money has basically been discontinued at this point, so there's no real guarantee it's going to keep working on Windows. Meanwhile Wine-HQ lists Microsoft Money Plus Deluxe Sunset as a "Platinum" level supported application, which means it should run essentially perfectly on any current Linux distribution.

Pick the distribution which seems the best fit and try it again. As Money is no longer being updated, support is only going to get better in Wine and worse on Windows from now on.

Even if you don't move to a different OS, since your data and Money are so important and Money is not particularly demanding in terms of hardware, it might still be a good idea to migrate money into a VM with a fully supported OS to insulate it from changes to the underlying OS. That would simplify backups, and guarantee that you can continue to use it essentially indefinitely even if you choose to use an ARM architecture Mac or Chromebook in the future.

Both VMware and VirtualBox are free for noncommercial use, available for all popular platforms, and allow easy snapshots and full backups. If you backup your VM to a cloud service you could lose literally all of your possessions in a disaster and still be in a position to recover everything onto nearly any computer within minutes.