Meghan,
If you can use MS Access on your Mac, I recommend it. I started with Excel, and moved over to Access for its ability to handle photos and queries. The export from my Excel file of over 500 crosses was easy. I have the ability to customize fields of course, add photos and generate reports. I am hoping to structure a report along the lines (generational) that you suggest, but haven't done it yet (no current need)
If you are at all technical, I believe that the out-of-the-box programs are limited and cumbersome to use. (Your mileage may vary)
The only reporting difficulty I have found is that there is a limit in the number of columns you can use in a report. Because of this, when I wanted to make a garden map of my various seedling beds, I had to make an export to Excel for this purpoose.
