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 and was curious about your experience, you said it was traumatic? Do you have any advice? And were you able to update to 2019 on your own or did you have to call the help center? I have been on the phone with them all day and no one seems to be able to help after being on hold for 2 hours. I would appreciate any advice you have, thank you!