I recently acquired Quicken Premier 2010. With the demise of Microsoft Money, Quicken seemed the obvious choice. I got the Premier version because I want to track my investments as well as my spending. My first impressions are pretty negative.
The biggest issue I have is there does not seem to be a safe way to import my bank account transaction data automatically. It doesn't seem like good security to give Quicken the id and password needed to access my bank online. This would not be necessary if I could download the transaction data to a file and then import the file into Quicken. However Quicken appears to have gone to great lengths to make this impossible. It is my understanding that they have done this so they can collect fees from my bank. This is pretty obnoxious and means I have been entering transactions manually which is painful.
The investment portion of the program has a number of issues as well. I would like to be able to enter a stock purchase in say 1985 (which I have not sold) and have Quicken automatically fill in splits, spin offs, dividends etc. This does not seem to be possible. The stock price look up only seems to go back 5 years and it does not appear to provide other information like dividends. This means the program does not seem able to provide an estimate of annual dividend income from a portfolio of stocks. There is also an issue with mergers. For example Wyeth was recently acquired by Pfizer. As a result all historical price information for Wyeth seems to have disappeared from their data provider (at least I can't figure out how to get it) making it impossible to track performance across the merger (without entering all the Wyeth price data manually).
In fairness it is possible that I will like the program better after becoming more familiar with it. However at the moment I am wondering whether I should have tried GnuCash first.