KeePass features an "Auto-Type" functionality. This feature allows you to define a sequence of keypresses, which KeePass can automatically perform for you. The simulated keypresses can be sent to any other currently open window of your choice (browser windows, login dialogs, ...).
By default, the sent keystroke sequence is {USERNAME}{TAB}{PASSWORD}{ENTER}, i.e. it first types the user name of the selected entry, then presses the Tab key, then types the password of the entry and finally presses the Enter key.
For sites or apps with weird forms you can customize the sequence.
The way OS X's "Keychain Acccess" handles this feels like a good compromise. After some timeout (a minute or so) the password gets hidden and you have to put in your master password to see it again.
- Set up dropbox on every computer I use.
- Figure out how to get keepassx to work on Android.
- Open up a password manager when I want to log into something. Oh, I can leave it open? Wait, is that secure?
- Figure out if there are any limitation of the password manager you've suggested, which you may have missed.
- Deal with a "password migration" if I decide to switch browsers, which will include an absolutely non-trivial search for some software that replaces an app that is now a crucial part of my daily routine.
I could go on, but password managers are most definitely not a trivial task -- they add a layer of friction that I simply can't bring myself to care about when it comes to security to my Gawker account. Computers exist to make my life easier, not as a creator of problems that require working around.