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I think it is neck and neck between Gmail and Outlook.com. They both have their pluses and minuses. The bottom line I think is if you are more wedded to Microsoft apps and services, go with Outlook.com, but if you like Google Docs, Photos, Keep, etc. stick with Gmail. Gmail's online offerings in Drive tend to be more collaborative. Their online document sharing works really well and you can simultaneously edit something with someone else in real time. Outlook.com's online document editing is more like the desktop apps (simplified) and less collaborative. Also, Android phones and Gmail go really well together. There are certain advantages to each one, but I say try both and see which you prefer. If you are signing up from scratch I think you only get 5GB of free space with Outlook.com but you get 15GB with Gmail. Both have good spam filtering, nice webmail interfaces (but different), integrated calendars and contacts, online storage and online apps for creating and editing documents, spreadsheets, etc. and they work with a huge variety of second-party services. Both are big, reliable companies that aren't going anywhere.
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