Hi, I am experiencing some of the same issues and I was hoping you could let me know how it went. I am also using QB 2015 for Mac and no longer able to import my bank transactions so that I can reconcile 2018. I know I need to update to the 2019 version but am concerned about losing data. Especially because I am not up to date with the reconciling. I then want to switch to QB online. What is the best way to make the upgrade to 2019? I can't seem to find it online and keep getting re-directed and put on hold when I call. I have to have my books reconciled for tax season so have to be able to download my bank transactions.