It’s been a few months since my first experience with Quicken, giving me a better idea of its capabilities and limitations. Unfortunately, it has more of the latter. One of the key features was its ability to download account information, but this only works for 2 of my many accounts and even then takes an average of 3 with repeatedly entering passwords and clicking past error messages. In all fairness, Quicken is only partially to blame; banks seem determined to make their logins more difficult in the name of preventing fraud.
Once your data is in Quicken, though, it does provide good aggregation across accounts. One exception is that it doesn’t provide an easy way to reconcile transfers between accounts, counting them - double - as “other expenses”. For everything else, though, you do get consistent categories and the ability to drill down to individual transactions.
In summary, I think Quicken has limited utility: occasionally aggregating offline data. It’s automatic download and bill payment are too sketchy for regular use, but I could see using it for crunching expenses and budgets a few times a year. For everything else, I’m more inclined to go back to the bank’s web-based bill payment and my trusty, extensible financial spreadsheet.
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