That's totally right. But you're not comparing apples to apples.
You say that users just have to accept that Linux is different. I agree with that.
But if you compare the amount of knowledge needed for just everyday stuff, like the dvd playing I've mentioned, the psx emulator, etc... then you can absolutely NOT claim that these things are easier in Ubuntu.
To give you another example. What OS would I choose when giving a presentation in school? Bare in mind that people giving a presentation are normally a bit stressed, so the least thing they would want is difficulties with their computer. Now, on windows, I just connect the projector and push Windows+P. Voilà.
On Ubuntu, I have to go to Nvidia X Server settings (so I have to know I have an nvidia card! Why should a regular user know that?), I need to change the settings to clone or whatever and then HOPE that it works. Because, that's right, sometimes for no explicable reason, I just get a purple screen and need to reboot.
If you claim that is a user friendly experience, then I hope that I'll never have to use one of your programs!
You want to compare apples to apples?
Windows 7 Pro out of the box does not play DVDs. Shocker eh? I installed windows 7 on this computer, and a few months later (After keeping it totally up to date) I got bored one afternoon and threw a DVD into the drive and went to watch it. Nothing. Windows didn't know what to do with the data, because apparently I never installed any software to do this. I had to remember that both DVD drives in my system came with Data Disks that had programs on them, then install the needed software off there.
But it doesn't end. A few weeks later, after I assumed I had all the related issues sorted out and that software up to date (In case you didn't guess, watching movies on my computer isn't a really important thing to me. That is what the DVD player and TV are for. I have work to do here dammit!) my sister sends me a DVD she made of my nephews. She lives on the other side of the country and I don't get to see the boys often, so it was a nice treat to randomly get that package. I throw the DVD into the drive.
I get some random error about missing Codex and stuff. An error message that made me, a software developer tilt my head to one side and make a WTF face for a few seconds before my brain kicked back in gear and translated the message. Half an hour later I had googled a few pages and finally figured out what I needed to install. You really think your Grandmother would have happily smiled and said to herself. "Oh, silly me, I should just google the codex, find the right files, and install them", or would it be more like "It is broken and I have no idea how to fix it."
Don't compare the experience of someone setting up Linux all by themselves and then trying to use it to the experience of someone using a computer with windows that was installed in a factory. It is kind of like comparing the experience of two people driving cars, where one person is driving a stock car off a dealer's parking lot, and the other is driving a kit car that started off as a few hundred boxes spread over their garage floor.
As for the display thing. Don't know what to say, the three times I've done it I've just plugged it in and the video port just started dumping a cloned screen. It wasn't an issue on my machine, but I can tell you lots and lots of issues computer science students have had with different windows laptops. Many of them not pretty, and all of them exceedingly frustrating.
If you want to talk about Windows user friendliness, why not talk about the experience many Window Users face when it comes to browsing the web? I couldn't tell you the number of times I have to use someone else's computer and their Internet Explorer "Aka, the Internet" has nearly half the window left to actually render the web pages in, after Yahoo tool bar, 20 'add blocking' tool bars, and all the other random junk malware that attaches itself to a core piece of their computer. The windows User experience is far too close to the windows Admin experience. And when you combine the two with an user without much experience in either, then
very bad things® happen. As opposed to Linux, where the user and admin is very clearly divided, an inexperienced user attempting to do admin things results in either them looking up instructions on how to do a task and becoming an admin, or running into a wall asking for a password they don't have.
Long story short: Both Windows and Ubuntu have shortcomings and major issues. Both require some advanced knowledge to properly do their related admin work. Once properly set up, both are excellent environments to work in.