Hi there, Iceguy.
Allow me to jump in and help provide some additional information about importing transactions in QuickBooks Mac for Desktop.
I've checked my resources to verify if there's an on-going issue about importing transactions in QuickBooks Mac, but we have no reports of any.
Also, QuickBooks Mac 2019 is the latest version, and it is compatible with the Intuit Interchange Format (.IIF) files when uses to import lists or export transactions.
To get started, here's how to download and install the .IFF import kit:
For additional reference, you can check these articles to learn more about the .IFF files:
If you need further assistance with the steps about import transactions, I recommend to contact our QuickBooks Desktop Mac Support Team. They have additional tools to pull up your account and do a remote session.
Here's how you can contact our customer support:
That should do it! Please know that I'm just a post away if you have any other questions about the .IFF files format. Have a good one.