Any way of making the login process less tedious?

The Shutdown feature is great, being able to bypass POL, but is there anyway we can get the equivalent of it when logging in and completely skip Playonline?

They did away with auto-login when they linked SquareEnix Accounts to PlayOnline. They did that because it was one way people's accounts were getting hacked. The SquareEnix Account system does not allow your password to be stored for auto-login anymore.

Before SquareEnix Accounts, you used to be able to save your PlayOnline password and set an account to log in at POL Viewer launch. You were never able to skip PlayOnline, and there are still some functions that you would want to boot into PlayOnline for, plus consoles MUST boot PlayOnline Viewer, as FFXI itself isn't bootable. If you want to pull screenshots off a console, you must use the email client built into PlayOnline Viewer. If you want to add people that are offline or on other servers to your friend list, you must use PlayOnline Viewer.

Is it impossible to make a launcher for PC that you simply put your details into, then it skips everything else after verifying they are correct and goes straight to the character screen?
If you need to use the features of POL, then you could use the original exe.

There's probably not enough demand for it.

Also, you can only link 8 characters/Content IDs to a PlayOnline Handle, so if you have more than 8 characters, you need more than 1 handle, since you can have 16 character slots. You can only change handles and link Content IDs in PlayOnline Viewer. The Friend List also uses PlayOnline Viewer, which is still running in the background without a window. A whole lot of the systems were designed to intergrate into PlayOnline Viewer back in 2002, and the original development team isn't present anymore, while the current development team doesn't want to mess with certain older code that they don't fully understand.

Remember, the original idea for PlayOnline Viewer was to be a hub, like Xbox Live or PSN, for PS2 online games from SquareSoft, Namco, and a few other companies. At its largest in Japan, it had SIX games using it (JongHoLow, Tetra Master, Final Fantasy XI, Dirge of Cerberus, Front Mission Online, and Fantasy Earth) that all required Content IDs, and you could message people playing different games that were on your friend list. You can have up to four handles, and 8 Content IDs attached per handle. Just because they removed games from service doesn't mean they changed PlayOnline Viewer. Every single game they had using PlayOnline had to be launched from PlayOnline, and it integrated into the messaging, email, and Content ID system PlayOnline provides.

It would likely be a pretty big overhaul of the backend systems to remove PlayOnline Viewer from being a requirement to launch.