Update: Windows Live Writer Portable
I'm still using Windows Live Writer Portable that I build a little while ago. I have discovered that there is an issue when you move the USB stick to another computer. When you try to publish your post you'll get a message box that an error was received and you won't be able to post.
I have tracked the issue down and it comes back to WLW storing your password in the registry. When it does this it creates some kind of hash. I believe takes some information from the current computer you are running on and encrypts uses that to create the hash. So, the password info is encrypted in the registry but is specific to that machine.
To work around this, before you start writing a post on a new machine you need to go to the menu bar and click Weblog - Edit Weblog Settings and enter in your password. Then click next through the series of setup screens. Note that it is just your password you have to redo. All your FTP and other settings will remain in tact.
If you restart the app on the same machine this isn't an issue as the information is stored back to the USB stick. Once you get used to it you'll know that you have to do it because when you start Windows Live Writer the editing screen won't show the style sheet from your blog.
You could actually have different, machine specific, reg files in the \PortableApps\WindowsLiveWriterPortable\
Data\Registry or your USB stick but that wouldn't be ideal because of the other settings that might get changed and then other things might be out of sync.
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