I started off doing basically the same thing (installed 19.0.0 in my MacBook Air running High Sierra and Quicken Premier (2019 R22.12) was fine. Then I did the same thing on my iMac (High Sierra), and it worked fine too. I then installed Catalina on the iMac and Quicken could not find my data file so it opened a window asking if I wanted to find an existing file, make a new one etc. If I clicked on "Find existing" Quicken froze and I had to force quit it. I tried this several times.
After checking around I found that my Documents folder had been in the root directory ("Macintosh HD) and the installation of Catalina moved it to a directory on my desktop called "Relocated Items > Shared." I moved the Shared folder to my Users folder. After playing round with it, I was able to use the window that opened when I started Quicken (find existing file, create new, etc.) to create a new file. That worked and then I was able to open my real Quicken file from within Quicken.
Anyway, all seems to be fine with Quicken in Crossover 19.
Jay
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