The only real advantage to, say, WordPress.com, is automated security updates, but that can sometimes break your site.

And that's why every self-hosted wordpress site I set up takes 3-5 hours, just for the security checks and enhancements, setup of automated update notifications & off-site backups. 

After that, your site notifies you by email, when it needs you to update something, at which point it's one click to make an immediate backup of database and all files, so you can roll back if the update breaks things, till you can figure out a solution.

I have become an expert in setting this stuff up.

I had the OP's best interests in mind: how to get your computer illiterate wife off your back, sorry, make her more independent  And surely it must be less hassle to just select a log-on and password and a theme on Wordpress.com, then to have to get into the whole business of downloading Wordpress, getting server space, uploading it, installing it, and then regularly having to update it (however much that appeals to DoCo's techie audience  ). It's just more work.

Which is why I offered to do most of the work for him if he wants my help. Then it's just a matter of picking a theme and setting up WLW for her, leaving the rest to me. 

and all I did was be a fussy beggar when it came to choosing a theme :-)

And he was so fussy that he abandoned all the other ideas when he saw the default theme that comes with Wordpress, and decided it was perfect for what he had in mind. 

But looking at all those other themes wasn't a complete waste of my time. My daughter found one she really liked a lot for use on her own portfolio site, if she ever finally decides if she really wants one or not, and I found a few for some other purposes of my own.

When I say 'setup', I mean everything from domain name to hosting to Wordpress plus a contact page (all free)

It wasn't entirely free. Instead of it costing him any money for my services, I did it in exchange for a small favor in the near future. 

Hmmm... I'd actually disagree.  If you want a dead simple installation... wordpress is as dead simple as it gets.  Now there's more behind the scenes as you add stuff on... but to get the basic themes up and running, even self hosted, you can do it with very minimal technical experience.  It just depends on who you get for hosting at that point.

I agree and disagree with Wordpress' simplicity to setup and maintain.

I agree that it's easy to install, especially on hosts that have Fantastico (or an equivalent) that offers 1 click installing.

I disagree in that properly securing it is a completely other story...quite complex, with having to deal with things like editing .htaccess files, knowing if you can relocate your config file, knowing what the error messages mean if you get any while configuring and running automatic offsite backups, knowing what to do if your hosting provider has blocked access to your login page "for security reasons" and being able to actually do it without messing your site up. Checking and fixing file & folder permissions, and knowing what each should be to protect your blog without breaking things. Knowing that you should create 2 accounts on your blog and never use the admin account for posting, knowing that you should delete the first account created so no account has a user ID of 1.

And for the infrequent blogger, keeping it up to date when you don't login very often to see the "you need to update X" messages, and not knowing how to set things up so your blog emails you when something needs your attention.

It's a 3-5 hour job to do everything and not for the faint of heart, non-techie, or wordpress newbie. But once done, it's quite secure and easy to keep everything up to date.

And yes, I did all of this that I could, and more, for the site I set up for tomos and I am managing it for him, so all he has to worry about is posting his images....I take care of the rest. I even made a bunch of sample posts for him to learn from.

And I was offering to do the exact same thing for cranioscopical, if he wants it, so all he will have to do is install WLW on his wife's computer and show her how to use it, which is easier than using AOL email.

But a simple out of the box install is very easy, if that's all you want or care about.

for easy...wouldn't squarespacebe the best?
http://www.squarespace.com/stories

squarespace is way easier than wordpress.  if wordpress takes hours to setup, squarespace takes minutes.  i'm talking full customization and everything.

Setting up your own domain should be recognized as a different beast from hosted solutions.
All or most hosted solutions like WordPress.com are basically sign up and 'Add new something' and a bit more for choosing themes for example.
As far as self hosted goes the WP installer is surely the easiest? with or without dealing with Fantastico type tools. Also with WP afterwards you need something like ftp rarely (often never) which adds another layer of complexity for the non-techy user.