I really hope you're joking. It has nothing to do with looking trendy. The operating system isn't even comparable to Windows. The way it indexes files, loads images, etc. are all on a different level then Windows. Please, provide me with specific examples in areas which Macs are lacking.
If you're willing to spend as much as the above computer, a Mac would be your best bet. I used to have a tendency not to like Macs just cause I heard long time Windows users talk down on them. They're honestly ridiculously better in every single manner. Why don't you want one?
I believe there's two separate forms of being "fluent" in a language. One is being able to hold damn near perfect conversation and/or understanding all the grammar, etc.
It's possible then you have a learning disorder. Don't let anyone tell you otherwise, they're real things. My friend had one and it caused him loads of strife until he finally got it checked out and it was actually classified by a doctor as a learning disorder. Now he has extra time on tests and...
Yesterday when I got my new Mac and I was registered a new Apple ID, I didn't have to enter any credit card info, simply an address. Nothing would have stopped me from putting a fake address.
I don't believe that the process is so complication. If you're headstrong and quitting actually means something to you, then you should be able to take the practical measures to stop.
Wordpress.com is the basic platform. They keep it hosted at subdomain.wordpress.com and you have customization limitations. With wordpress.org, you download the platform and you can do whatever you want with it.