Alright Hound 3, prepare for a healthy dose of me! I don't mean any offense, I'm just writing my thoughts so please don't take offense.
Mechanics:
Something about the flow of the first paragraph throws me off. I think it sounds too much like how you would speak verbally, which may not be bad, but in this case I just feels awkward... but I can't quite put my finger on it.
Period at the end of "...give Microsoft a try" and the smiley face might want to be removed depending on how formal you want to make it.
And you may want to put the lolololoololol sentence in "quotes"
Try to get someone to fix up your flow throughout. Right now it's not the most pleasant to read because of the formatting and density. (but its not bad!)
My apologies, I can be picky so don't take anything personal.
Other:
I thought Steve Ballmer focused on both consumer and enterprise and the products put out weren't exactly glitchy but just awkwardly managed or handled. I think the Surface Pro 1 was a great execution, just hampered by the chips inside at the time. (battery life) WP7, WP8 , Windows 7 and Windows 8.x were a whole lot less quirky than 10 today.
1. Email
To be honest, unless I'm mistaken both Google and Microsoft use automated tools to scan for keywords in emails. You're implying Gmail is inferior to Outlook.com in regards to privacy. There are a lot better options if privacy is a top concern by the way. And I believe there are also antivirus options in Gmail. Neither company is really safe for those worrying about the NSA and other government big brother shenanigans.
The blocked senders feature is also hardly a reason I personally would switch. As far as I know it doesn't matter whether it ends up in spam or just vanishes.
I would emphasize ad placement between the two services perhaps.
Also when I switch to contacts and whatnot in Outlook.com I'm pretty sure it loads a whole 'nother page too.
What I would mention, and that's just me is compatibility. Exchange ActiveSync has been around a bit and it works with a lot of devices. I can sync my Outlook.com with my old Palm OS PDA and webOS phone while Google is a straight-up no go.
IT also lets you get push email on an iPhone, while Gmail can only be polled every 15 minutes at the fastest on iOS.
Aliases are also a plus. And you have the option to pay for Ad-free Outlook I think. And maybe you can talk about the video you attached too.
2. Search engine
This is very subjective. When Bing fails, I usually found Google to have something a bit better - unless it was something neither search engine could find. I won't be able to convince someone to switch to Bing by saying its "far superior." I don't believe that claim myself. I think the best you can do is to ask people to just try it.
Talk about the superior image search UI though, and also the video preview feature when you hover over the link. That's an old screenshot btw.
And also how it can kinda sync up with Cortana's interests. And those cool squares that appear with facts over the background image. And the bar that appears at the bottom with other news related things.
3. Office
I think you can emphasize the free Office Online web apps as direct competitors to Google Docs. Complete with live collaboration. (although it didn't work that well last time I tried)
Say how Office is the standard for office suites worldwide.
4. Yep. Keep is a lot simpler, which works for a lot of people.
Emphasize how OneNote is terrific for students, notetaking and generally holding everything.
5. As for browsers, you may want to go all the way. See what I said about Bing. Might want to get someone to try Edge but yea.
Go Firefox.
6. I got nothing.
No need to call yourself picky 
Facebook
Twitter
Instagram