Thank you for reaching out on the community and telling us about your issue. I do apologize for the late response.
It sounds like it makes you select your file each time right? To do that you normally go up to file -> Open Recent? Does it load in properly once you're able to get it opened or does it give you issues? If you are able to use it could you try moving the file and see if you're able to get it to load each time you open the program? You can move the file by going across the top to file -> move to. From here try closing and reloading quicken again to see if we're able to load in properly to the file.
Please try this out and let us know how it goes!