I've been a Quicken user since way back, probably early 1990's. One thing that I liked in the old (I mean like 2013 or so) Quicken versions was the ability to really understand my investment returns. I could create a report that showed my return on investment for a specified period of time, so I could easily understand how my investments were doing. I don't find that report type in the modern Quicken Classic for Mac, and hope that it is implemented at some point. (I am self-employed and each year I'd use a report like that to determine where I'd put my annual SEP-IRA contribution. I'd create a report showing my various investment returns for the past year, then base my contribution upon that. Due to dividends, dollar cost averaging, etc, it is more complicated than just comparing how the prices changed over the course of a year.)