I have used Gmail for years, it has always been the best of the major email services out there. It had the best search, a great filter system and it was fast.
Times have changed though. It's search doesn't work like I expect it to. I've searched for several product licenses that I know exist in my Gmail, but can't find them. I know they exist; I migrated my email over to Outlook today and found them instantly. It's forced me to use apps like Evernote and 1Password to save that information.
Gmail's filtering is to complicated. I know it's powerful, but I find myself searching google for how to perform a specific filter because I can't figure it out. I tend to get frustrated and move on without finding what I was hunting for.
Google uses a label system that's very confusing. I can apply a label called "Work to an email and then move it into the same "Work" label like it's a folder. I understand that they do it for flexibility in filing; make it easier to store the same email in more than one location in your inbox, but it's really annoying and frustrating when you have thousands of email messages and you still can't find what you're looking for. I know some people will think I don't know how to file properly, and maybe that's true. If it is, come and show me how to properly organize 10,000+ emails with labels and then dig through the emails associated with a label or two to find the content you need. It's not easy.
I also don't like the whole
all mail thing. When I delete a message, I want it deleted. If you want to "archive" it then fine, but don't include it in the stupid
all mail folder. I deleted it so I don't see it again. I apply labels to things I want archived. Archiving every single piece of email that I receive is just stupid.
Lastly, Google had Google Apps Standard; a free service for those that wanted to use a custom domain and have access to some of their Google Apps items. In December of 2012 they removed it. Just like a lot of other great things they've removed. I want a personal domain associated with my gmail without having to provide people my gmail account and I don't want to deal with mail forwarding. To be honest I was a big angry that they got rid of that feature unless you are a business and pay for it. I have no problem paying the $5 a month for the Business Google Apps except that I already pay it for my business and and don't want to setup an account using a "fake" business just to use it personally.
On top of that, their UI and service features hasn't changed much, with the exception of how they scan my emails and deliver targeted ads. That's improved.
So I gave up. It's time to pack up all of my email and move on.
Let's be honest, Hotmail and Live sucked. Really bad. It was full of spam and my hotmail account was hacked like 4 times. However, just like Google, things have changed with time. For Outlook it seems to be for the better.
The first thing I did was use a feature that I was not aware that Microsoft offered. The ability to use your own custom domain with a Outlook.com email address. This worked really nice! Not only was the process extremely easy to set up, Microsoft provides my custom domain with 50 free email addresses that I can use. This really helps me out, as now I can have my personal email address as something related to sullinger.us and I can have a support email address at firstname.lastname@example.org. The nice part here is that I get the same thing that Google Apps Standard was offering when it was free, prior to them going business only.
The next thing I did was import all if my Gmail email into it. The import process took a lot of time. By the time of this writing, it had been importing for roughly 6 hours. Luckily, this is a server side process; I don't have to sit and not close my browser. I closed my browser and let it import. I have a ton of Gmail emails, so this is to be expected.
The sweep feature of Outlook.com is really nice and I can see it really improving my ability to get to inbox zero. I can select an email and tell Outlook.com to move all emails from this sender to a specific folder, delete all emails from this sender, schedule a clean up or create a rule from this email. Using the sweep feature, I was able to re-organize about 1,500 email messages imported from Google (it's still importing) in under an hour. It's really impressive how productive one can be with a tool like this.
The last thing that I really like about Outlook.com is that it uses the Exchange ActiveSync server for clients to connect with. This means that I actually get real push on my iOS devices. Something I do not get with Google. Instead, I have to pull new mail down the from server every so many minutes (chosen) or manually. It's annoying.
Migrating from email services can be a real pain. I'm currently focusing on just migrating from Gmail for the time being. However, once the import process is completed, the emails are organized and I have refreshed the sites I visit that use my Gmail email, I will probably start the import process on iCloud. I like iCloud as a service, but it lacks way to much functionality to be a good email service.
I really like having my contacts in iCloud, along with my calendars and tasks. Unfortunately, Microsoft and Apple haven't worked together to get iCloud to work on OS X's version of Office 2011. So I have to decide if I want to move my contacts and calendars to Outlook.com as well or just leave them in iCloud. Moving my email to Outlook has made it a pain to email contacts, as I can't get my contacts from the OS X Contacts app over to Outlook 2011, up to Outlook.com. I don't want to sync my tasks with Outlook.com because then I would loose the ability to use Siri. So it's not a perfect solution just yet. Odds are I will migrate my contacts and calendars to Outlook.com, but I haven't 100% decided yet.