Investments are done through TD Waterhouse. I would rather outsource tasks rather than hire someone. Nothing fancy, just some simple performance reports. All three software clearly accomplish that. Second, ease of use is important.
Customer support is also equally important.
Must be easy to reach and solve problems quick. And finally, the company must be solid so that they are around for years and not vanish suddenly. The reason is I got in their recent promotion where they are giving away their 2.0 Windows version for free. The company is solid with a long history in the industry. It is more than portfolio management, it has contact management features that I sure can use.