Microsoft Hotmail

Pros: Great web user interface, great device compatibility, excellent performance, integration with other Microsoft products and services

Cons: Lacks two-factor authentication

Rating: Four out of five stars

Recommendation: For cloud-based email, contacts, and calendar services, Microsoft has two big offerings: Hotmail and Office 365. Hotmail is the better choice for most: It offers an efficient web interface, works with Windows Live Mail and Outlook on the PC desktop, and is compatible with virtually any mobile device. Where Hotmail falls short for some is in two key areas: It lacks the high security of two-factor authentication (see Gmail). And for aggregated email accounts through Hotmail, email sent as if from another account will bear an "On Behalf Of" header betraying your Hotmail use and making some spam filters skittish. But given its consumer bent and general performance benefits over Office 365, I give it the nod. It's what I use.

Contact: Microsoft

Discussion: Paul's SuperSite for Windows: "What I Use: Hotmail and Exchange for Email"  and "From Gmail to Hotmail: An Update"

 

Microsoft Office 365 for Individuals and Small Businesses

Pros: Offers powerful Exchange-based email, contacts, and calendar to the masses inexpensively; SharePoint Online collaboration features

Cons: Lync Online lacks many on-premises features; it's not free; configuration can be difficult; adding Office 2010 Professional Plus is expensive

Rating: Four out of five stars

Recommendation: Office 365's Plan P, the version for small businesses and IT pros (i.e., individuals), offers the right price: $6 per user per month. But even at that low price, Microsoft is competing with rival free schemes. If you can get past the price, and the hurdle of configuring the service—hint: employ a Microsoft partner for this—Office 365 is pretty incredible. You get Exchange Online–based email, calendar, contacts, and tasks management. You get SharePoint Online–based document collaboration, and a private version of the Office Web Apps. And you get a limited version of Lync Online. If you add Office 2010 Professional Plus through the service, it costs an additional $15 per user per month. I'd like to see less expensive options and simpler configuration, but it's still great, especially for small businesses.

Contact: Microsoft

Discussion: Paul's SuperSite for Windows: "Office 365 for Individuals and Small Businesses"