
With more info about what version you have and what computer you have access to, we can discuss possible steps forward. So I can't attest to the functionality of the automatic aspects of bringing in investment and/or financial information from investment companies/brokerages and banks/credit unions. The short answer is that the current Quicken Mac cant open a data file from 2000. My needs are rather basic with all my data in puts done manually.

The bottom line is that I'm now using Quicken 2017 routinely with no problems so far. But I'm getting upon the learning curve quite quickly. I'm still getting used to Quicken 2017 since there are many user interface differences from Quicken 2007. But unlike Quicken, Banktivity is designed specifically for Macs and remains a very popular and robust personal finance app on macOS. Intuit Quicken 2017 v4.6 for Mac is a professional application to manage all the personal finances and provides a variety of powerful tools to manage the income. Quicken 2018 for Mac and later versions have now caught-up somewhat and unfortunately the latest version of Banktivity 8 is, like Quicken, subscription only.
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Quicken technical support guided me through the whole process and even gave me the Quicken 2015 update I needed at no cost. Download Quicken 2017 v4.6 for Mac free latest version offline setup.

To successfully migrate my data, the update had to be done in two steps: first migrating from Quicken 2007 to Quicken 2015 and then from 2015 to 2017. Installation was a hassle, however, because I was updating from Quicken 2007. That is, any transaction that is not income or expense, just the movement of money from one account to another.

Loan amortization, 2-line display, QuickMath, or are not as fully developed. A transfer is a special transaction used when you are recording a transaction between two accounts you track in Quicken.
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Considering that Quicken 2017 is not the newest release, I would have expected the price to be lower than what I paid. I suggest that you make sure that Quicken 2017 for Mac will meet your needs, since it is not an upgrade from QM2007 but rather from Quicken Essentials (which was re-written from the ground up, starting in 2010), so there are some features that are still not there e.g.
