Connecting to your bank over the Internet is exquisite. I travel all over the world, but as long as I have Quicken on my laptop, I can check balances, pay bills and transfer money between accounts easily. Getting logged on can be problematic, but the blame there lies with my bank and not with Quicken. Quicken's investment accounts make keeping track of mutual funds easy. You can even track investment results online.
Memorized transactions save a lot of keystrokes.
As you type the first few letters of a payee into an account register, Quicken will automatically fill in the rest, allowing you to use the info as is, or modify it before entering the transaction. The Windows application is excellent, and getting around the program is easy and flexible. The only big beef about Quicken will be heard from those with some bookkeeping background. It's not a complicated system, but it may be confusing to the average non-bookkeeper, so Quicken does not use it. Instead, they divide accounts into two different types.