How does Drupal lend itself to learning from scratch? I've got experience installing and setting up Worpress, Movabletype, Gallery1 and 2, and PHPWebsite.
If you've got experience setting up those other programs, then I don't think drupal will pose you any problem.
Do you think Drupal is comparable to these programs in terms of configuration and use?
Not sure. I've only used Gallery2. Gallery2 was a bit more complicated.
I also noticed they are in the midst of doing a version upgrade but only have the betas available yet. How are the upgrades usually handled. Simple file replacements?
I've not tried the latest version, but upgrades are usually simple file replacements, even across major releases. They're getting easier with each version. You normally have to run a DB upgrade script (via a PHP page, so it's not that hard) after replacing the files.