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Sync Mac <-> Online <-> Windows versions

I have been using the standalone versions of Quicken for Win for decades. I've never used the online features, as I'm living in Europe, only manual accounts.
Few years ago I moved partially to Mac, but kept my old Windows Quicken using on a virtual machine. Also I used another Quicken on a Windows machine for reports printing and used same file through a dropbox folder.

Now I (maybe prematurely, without reading this forum) decided to jump to the 2019 version and chose the Mac install. After my file was converted, I discovered that the reports are next to unusable - mostly that for some reason I cannot do multiple currencies in a single repoirt. Then I found that there is no way back to windows. My new file is not compatible (why a SQL database cannot be opened from both Mac and Win???) and the export functionality is unreliable and restricted.

So here is what I think as a workaround:

- There is no restriction for installations on Quicken, as long as they are on a single ID. So I install one on my Mac and one on my Windows
- What if I sync my new Mac Q2019 file to the online service - (already done, although I have doubts as in some places it shows $, where I should see €)
- And then sync again FROM the cloud TO an empy windows file?
- Will those versions then, trough the online sync of accounts be in sync (so I can continue running reports from the Win version and do my daily work on the Mac)?

Any ideas for stoppers?
I seem to see only that the history on the online account spans only two years, but I can live with that.

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