I went from a fully MS Office company, to a different company that used Google Apps, which was recently bought by another company that uses MS Office (that we are now moving to). I've had extensive experience with both products at this point.
===Outlook vs Gmail===
Outlook has a lot of things going for it. One of my main complaints is the functionality difference between the PC and OSX versions of Outlook. Outlook on the Mac just isn't as polished and is missing a number of features that the PC version has. On the plus side of Outlook, it has much more powerful searching/sorting abilities. You can sort messages by a large number of fields. Searching allows you to filter on different fields as well. The big part of searching is that Outlook will do substring searching (gmail will only match on whole words).
Gmail excels at labels and visual presentation. As it is geared towards the basics that a user will need, a lot of data that you just may not care about is hidden away. This makes the bulk of what is important more visible. Also, I feel it presents long email threads in an easier-to-follow manner. Plus, once you learn keybinds in Gmail, it works the same on PC and Mac (which is totally different for Outlook). The other big plus for Gmail is proper handling of HTML. Outlooks HTML engine is pretty atrocious.
Calendars: both are pretty comparable to one another. Outlook is nice as you get desktop alerts even with Outlook closed (google can do this with the 3rd party apps). But Google is nice in that you can set multiple people as being able to edit/update an event, so management of events can be easier.
=== Word vs Docs ===
I'd say the only way Google wins in this is collaboration. Being able to work on the same document with multiple people at the same time is such an amazing feature, I'm sad to lose it. But at the same time, there is so much that Google Docs just can't do. So much advanced formatting, numbering bullets, and layout that it just isn't all that great at. If you just need simple documents, Google Docs can handle it, just don't expect anything too fancy.
=== Excel vs Sheets ===
Sort of the same argument as Word vs Docs. Collaboration is amazing in Sheets, but it misses a lot of advanced functionality and formatting. It's ok for basic stuff, but don't try to do anything to advanced.
Funny enough, in this category I feel Apple's Numbers is a really great tool. The D&D game I'm part of uses a Numbers sheet to handle characters, and one of the big features I like is embedding multiple tables into a single view (something Excel or Sheets can't do).
=== Powerpoint vs Presentation ===
Powerpoint again is similar to the Word vs Docs argument. Collaboration is the one main feature Google wins at. Google Presentation has 2 major issues for me: 1) it doesn't auto-resize text if you go beyond the size of the box (it just overflows). 2) layout of slides can slightly differ between edit view and presentation view, which can be very annoying.
=== Word vs Docs ===
I'd say the only way Google wins in this is collaboration. Being able to work on the same document with multiple people at the same time is such an amazing feature, I'm sad to lose it.
You can collaboratively edit Word documents in Word 2010 and SharePoint:
Office 365 Word does it without the need for SharePoint (both in the Word web interface and the Desktop app). It's terrible, I can't recommend it. The number of crashes and sync-losses we had was ridiculous.
===Outlook vs Gmail===
Outlook has a lot of things going for it. One of my main complaints is the functionality difference between the PC and OSX versions of Outlook. Outlook on the Mac just isn't as polished and is missing a number of features that the PC version has. On the plus side of Outlook, it has much more powerful searching/sorting abilities. You can sort messages by a large number of fields. Searching allows you to filter on different fields as well. The big part of searching is that Outlook will do substring searching (gmail will only match on whole words).
Gmail excels at labels and visual presentation. As it is geared towards the basics that a user will need, a lot of data that you just may not care about is hidden away. This makes the bulk of what is important more visible. Also, I feel it presents long email threads in an easier-to-follow manner. Plus, once you learn keybinds in Gmail, it works the same on PC and Mac (which is totally different for Outlook). The other big plus for Gmail is proper handling of HTML. Outlooks HTML engine is pretty atrocious.
Calendars: both are pretty comparable to one another. Outlook is nice as you get desktop alerts even with Outlook closed (google can do this with the 3rd party apps). But Google is nice in that you can set multiple people as being able to edit/update an event, so management of events can be easier.
=== Word vs Docs ===
I'd say the only way Google wins in this is collaboration. Being able to work on the same document with multiple people at the same time is such an amazing feature, I'm sad to lose it. But at the same time, there is so much that Google Docs just can't do. So much advanced formatting, numbering bullets, and layout that it just isn't all that great at. If you just need simple documents, Google Docs can handle it, just don't expect anything too fancy.
=== Excel vs Sheets ===
Sort of the same argument as Word vs Docs. Collaboration is amazing in Sheets, but it misses a lot of advanced functionality and formatting. It's ok for basic stuff, but don't try to do anything to advanced.
Funny enough, in this category I feel Apple's Numbers is a really great tool. The D&D game I'm part of uses a Numbers sheet to handle characters, and one of the big features I like is embedding multiple tables into a single view (something Excel or Sheets can't do).
=== Powerpoint vs Presentation ===
Powerpoint again is similar to the Word vs Docs argument. Collaboration is the one main feature Google wins at. Google Presentation has 2 major issues for me: 1) it doesn't auto-resize text if you go beyond the size of the box (it just overflows). 2) layout of slides can slightly differ between edit view and presentation view, which can be very annoying.