I’m sure you, like myself, have a few hundred passwords which I use on a fairly regular basis. I sure hope that you shy way from a single password across all sites or a template based password where you reuse the same password but switch up a single digit or two. Both of which are generally considered a very bad idea, especially when dealing with your online banking or similar sites.
In the past, I tried to move my entire life and toolset onto a Pen drive. I have had a varying level of success across the board with it failing miserably with the larger tools like Visual Studio, Microsoft Office, and similar applications. Typically those that have a heavy dependency on the registry. In my perfect world everything would be local configuration files -this push to the registry (away from ini files) was a mistake IMHO.
For the longest time there was really only a single solution in the marketplace for reliable and safe Password Management tools. That was RoboForm from Siber Systems. It was so vital for me that I purchased their USB Version “RoboForm2Go”. Over these past few years it treated me quite well and I still highly recommend using it for those that want an offline/portable installation-free solution. For example if your one of those paranoid (safe) types that don't want some external site hosting your credentials…
A few months ago I realized that the majority of my daily use of my “Portable environment” was specifically for RoboForm and nothing else. The ole 80-20 rule applies. I took a good long look at that fact and decided that I wanted to minimize the hassle of carrying around the USB Pen drive, getting it running, etc.. on a daily basis. I also noticed that I would have liked to share this data with a few machines, simultaneously. This forced me into looking into an online solution. At a minimum it would plug into Firefox and store all passwords (safely) on a remote site; and be reliable/available 24x7. A colleague recommended me to check out LastPass. Since this met my minimum requirements, and then some I decided to give it a run for its money.
I can safely say that I have managed to completely make the transition to LastPass with no issues. The online service is extremely reliable and their FireFox and IE integration is stellar.
I also find myself using the Windows Mobile version of their product. It needs work but it provides easy access to my data with a few clicks – you will need to upgrade to their premium product for this to work – its only $1 per month and you get a bunch of devices supported plus a few other “features”.
Great job done by the LastPass team.