I've been using different OS's for over 30 years and don't understand what this hubub is about. The last time I had compatibility issues was Excel to Excel, and it had to do with Macros. Which I have no need for. I don't worry about what app I'm running, I just worry does it support standards. When the answer is yes there are few issues. When the answer is no then it is relegated to the "only if I have to" pile. I have accounting apps, word processing apps, I have never felt the need that I must have Windows, Mac or what ever. From million dollar transactions to the first pictures I digitized 20 years ago. The computer with the OS is a tool. I stick with standards and I have no issues experiencing the real world.
If you are tied to Quickbooks good for you but it's too limiting for me. Office 365? once again too proprietary for me but I have not yet once needed it. My current solution works perfectly for me.
It's like the QIF files from a bank. It works great when you are on top of things and becomes a pita when things don't work out. If you are on top of things then you don't need the QIF file because the bank rec is balanced before the bank can issue the official statement with the QIF file. My accounting app can process QIF files but it's more of a waste of my time.Try dealing with 1000 or so daily deposits from various POS systems with a QIF and you will understand what I mean.