Scoble just announced that he is switching from Hotmail to Gmail. From time to time as I hear people making the switch I go back and revisit each site to assess capabilities and see what I am missing. So far I have not seen a compelling reason to change from my 10 year old Hotmail account. I have had a Gmail account for a year or two now. So below I snapped some screen shots of the interfaces to talk to the advantages of each as well as to what I don't like about them.
The first two screen shots are of the message listing screen. Windows Live looks better. It looks more polished. I like the message reading pane on the right (you can also put it on the bottom). I couldn't find an option to do the same in Gmail which is a major disappointment because being able to arrow through my emails and scan them in the reading pane is how I work through my email.
I like the conversation grouping that Google has. That is a great feature to help reduce the size of email in your inbox by collapsing those ongoing conversations.
I am not sure what I think of the archiving of Google Talk conversations automatically. I think it is cool that I can do that, but the fact that it does it automatically for all my conversations seems a little much. I would imagine I could turn it off (just checked and yep I can). Windows Live Messenger allows you to save conversations to a file or email them to yourself on a conversation by conversation basis which I like (although you can also configure it to automatically save conversations to a file). Windows Live Messenger so dominates Google Talk in features though that it isn't much of a comparison and I am not meaning to compare them right now anyway so I digress.
Hotmail does folders and Google does tags - but both allow searching across your whole inbox on search terms which is way more important. I have largely stopped filing my email anyway with the pervasiveness of search these days. It is so much easier to just search and find what I need. That perhaps gives Google the edge here in that I can annotate a message with a tag describing it more directly if I want and then archive it to just get it out of my inbox.
I like the ability to right click in the Hotmail interface and get a custom right click menu to interact with a message.
Both services have way more email storage than I need (both Hotmail and Gmail have in the 5 to 6 GB range although with my Hotmail Plus subscription I get 10).
This view is where I look at it and can't believe all the love Gmail gets. The ads down the side are just an annoyance. I am assuming that most people must ignore them and learn not to see them. Additionally they are reading the content of the email and providing ads based on the content. While I imagine there are instances where this might be useful and interesting this feels very intrusive. To test out the length that this goes to I sent an email to my wife with the message, "Hey sweetie - can't wait for the romantic evening tonight!" Google's ads when I viewed the message in Gmail were nice enough to me provide links on how to get my ex-girlfriend back as well as where I can buy thongs and g-strings. Nice. Perhaps people don't pay enough attention to the ads to care or perhaps as some have suggested people don't care about their privacy as much such that having an email service read your email matters. But for me reading my email to provide context sensitive ads crosses the line.
I had to add a picture in of the Windows Live Mail desktop application for Windows that is also available. It is a lightweight desktop mail client which is more than enough for most consumers (your average home user doesn't need Outlook in my opinion). Of course with Gmail's IMAP and other support I am sure you can plug into any number of mail apps out there (and of course you get Outlook support with both).
Conclusion
In addition to the good things above I noted about Google - Google Calendar is better today than the Windows Live equivalent. Windows Live needs to get rid of having two different calendars - hopefully the next release of Windows Live Calendar will kill MSN Calendar and bring Windows Live Calendar up a notch. I like the way I see Windows Live Calendar going if it simply added true iCal subscription support not just the ability to import it would likely have all that I need.
Each service has it's strengths and weaknesses, but Gmail certainly doesn't yield a compelling reason for me to switch. Plus when I look at the overall platform (Windows Live versus Google) I believe Microsoft has made great progress in establishing what Windows Live truly is and has begun to build out the platform effectively with things like Windows Live Events, Office Live Workspace, and Skydrive. I am anxious to see what MIX brings in terms of Windows Live announcements. Things have been a little quiet on that front lately and I am anxious for some new news.
Google feels like they are stuck in the mud right now in this space. I haven't seen any meaningful changes for what seems like a year. I am sure that I am forgetting something they have done - if I have please note it in the comments as I would like to know. Google's greatest strengths in my opinion lay in Google Calendar, Google Reader, and their main search page. The main search page does little to tie me to a platform honestly - I can be Windows Live based - have a Google search bar in my browser to do web searches and I have the benefits of the web search I prefer with the productivity platform (Windows Live) I prefer. I can see why people prefer Google Calendar, but once Live Calendar gets true iCal subscription support (they already publish in iCal effectively) than I think the advantage goes away there.
Google Reader becomes for me the most compelling piece of Google's platform. I will not switch from it until something can come close to what it does. The starring and sharing (especially sharing) is a key part of my feed reading workflow (although for the casual reader of friends and family blogs they likely would matter very little). I can't believe we haven't seen any integration between Gmail and Google Reader yet. For my family members who aren't super techy, but want to read blogs enabling them to subscribe to RSS feeds and have them show up like emails in their email (which they religiously check) is huge. That would be a huge boost to the adoption of RSS and Atom. Today most of them use Windows Live Mail (that is the desktop client for Hotmail) to read their mail and it allows subscriptions to RSS feeds so I enable in there the subscriptions to blogs of friends and family and they are off and running. Simple and seamless. My grandma and grandpa read their grandkids blogs through RSS that way which is more RSS than most of my coworkers take advantage of!
