Like you, I prefer outlook calendar to google when on the PC. However, I also want to access and update my calendar(s) from anywhere and grew tired of the unreliable syncing of trying to get outlook to sync down and up to google. Usually I'd come up with some 3rd party software that would work for a few days or weeks then it'd invariably become glitchy.
So now I use google calendar and sync my work outlook up to it (I don't even try to sync gcal down to outlook anymore since that was infuriatingly difficult). I've found that there are wonderful calendar apps for Android, my fav is Business Calendar. These make gcal more than tolerable. So now I have all my calendars(work, 3 personal, 3 shared, several more reference) on gcal and am not looking back.
If you REALLY prefer to stick with using outlook as your main daily driver, then I would consider paying for GOOD syncing software to make it painless, especially since you want contact syncing, like Companion Link or something. You CAN go cheap with outlook sync software or find free workarounds (believe me, I could write a book), but if you have to keep tweaking, fixing, and resetting your calendar syncing once a week or so it will so NOT be worth the money saved. Otherwise, you may want to consider getting a windows phone instead if Office syncing is top priority? I really have no idea if WinPhone is better at this but would be shocked if it isn't!
I am carrying a BB Curve (work) and Droid 3(personal) right now. Sometimes I reach for the BB for quick messaging....but EVERYTHING else about it feels archaic compared to D3. I used to see my mobile (several treos and BB) as a backup interface where I could fumble around with basic calendar and information management if I HAD to in a pinch. It'd just be a crappy substitute for a real PC and browser. Now with the huge screen, there are several things that I just do on the Droid and not anymore on a big computer. Calendar, tasks, notes, finance are a few of these things. The main interface is now the always-with-me handheld. So having that stuff SEAMLESSLY in the cloud way more important to me than it used to be. Google, evernote, wunderlist, etc are built for ubiquitous access. Outlook/OneNote are a superior interface but lose bigtime on being the same on every device all the time. Until they fix that I won't go back.
So think hard about if you will see your phone as just a 'snapshot viewer' of your core experience on your PC... or if it might turn out to be the other way around.... If the latter, you will be far happier with ubiquitous tools and not constantly having to fumble with keeping your things 'synced'.
Having said all this I AM a big MS fan and think OneNote is perhaps the best program ever created, especially with it's Outlook connectivity. It's the pinnacle of how great note-taking/email/calendar/task management. But I've been hoping for years that it could live well outside of my PC and right now it can't. Not yet anyway...if they ever get OneNote to sync like Evernote can then I might go back.
But right now I'm loving Android and the hundreds of ways I can find to build a good alternative that is always in my pocket.
Some calendar notes for you:
-Windows Live/hotmail has a pretty decent outlook sync that you can install for free. Once your calendar is 'in the cloud' on windows live you can 'subscribe' to it with other cloud calendars like google's. I keep referring to google because if you get an Android phone then you'll most likely want that as opposed to yahoo, live etc because of all the native integration.
-I currently use google calendar sync to send outlook calendar up to google, but not two way. It can sync down, but that has caused trouble for me.
-I love seeing multiple calendars in one layered view. Outlook is awesome at this, but so is google. I've found that it is VERY difficult to make this happen on Outlook with outside calendars in a reliable way. Like syncing to and from anything but your 'main' outlook calendar to the cloud is trouble unless you want to pay for really good sync software. So I gave up on that and just have one calendar on outlook and sync it 'up' to google...so my multiple calendar view is now in my browser, not on outlook, but I can still play nice with outlook's calendar at work.
-You referred to color-coding your calendar. If you are talking about different types of things on ONE calendar than a good alternative might be just having multiple calendars instead of multiple categories. Then you can toggle on and off and colorize just fine. Now that layering calendars works well, it can fundamentally change how you look at using your calendar in general and make it much easier to share calendars. Gcal makes for uber-easy calendar sharing and subscribing. It's been a long time since I accidentally listed a personal appointment as 'not-private' so the wrong people saw it. One less thing I need to consider when creating a new calendar entry. That kind of crap happens when personal and work events are on the same calendar. Just keep a whole different calendar for each role/purpose and the sharing and privacy is automatic.
Sorry about the long response, just wanted you to know that I feel your pain about outlook and have been on this journey you are about to begin for a while.
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