I’ve always been a heavy-duty user of both iCal and Address Book. If something doesn’t get entered, it doesn’t happen. I put my wedding in iCal, for crying out loud - complete with an Event Reminder that morning (in case the hangover I would earn at my bachelor party was enough to erase my mind).

In college, I was a Newton user. It synced with iCal and Address Book very well, most of the time. I also used .Mac (sounds retro now) for email and backing up my contacts and calendars to my iDisk. After the Newton, I used a Treo in the 8 months leading up the iPhone launch. The Treo ran the now-defunct Palm OS on a Palm Treo 680. It synced with my Mac using mark/space’s Missing Sync software - again with .Mac in use for email and backups.

Then the iPhone launch. I jumped on board as soon as possible, and synced like everyone else for a long time - over USB.

When MobileMe came out in the summer of 2008, I started syncing over the air with my contacts, calendars, bookmarks, and of course, email. While rocky at the beginning, MobileMe eventually ran fairly smoothly for me, even as I added two more Macs to the mix.

In the past, I used my other devices to sync directly to iCal’s To Do list, but MobileMe doesn’t offer To-Do syncing. In fact, the iPhone (before 3rd party apps) had to no task management program, unless you count the pitifully weak Notes app (which doesn’t sync with Mail, even though Apple had said it would at one point).

When Apple announced the SDK, I was hoping someone would make a kick-ass task management program that would sync over the air with an on-line service. I settled on Remember the Milk. There are a handful of apps in the App Store that sync with it (including one written by the RTM gang, which I use) and their web interface is clean and easy. RTM has become the epicenter of what I do - in conjunction with iCal, I’m getting way more done and getting yelled at by fewer people.

Everything was smooth sailing for a while, until I had a couple of weeks of on-again/off-again service with MobileMe’s email that caused me some issues. So, I switched to Gmail, and set my MobileMe email to forward automatically. Gmail’s web interface is nice and simple, and the uptime is far better than MobileMe’s. Also, Address Book can sync with Google contacts, so I have my contacts on Gmail and my local machines.

Additionally, I can load “gadgets” in Gmail’s sidebar, so I can chat (with AIM and Google Chat), and manage my RTM tasks all looking at one place - my inbox. I’ve taken what used to be spread 4 applications (iChat, Safari, iCal and Mail) and put them all in one tab in Safari. And I live in that tab everyday.

So why even use MobileMe? If I could, I would drop MobileMe, setup iCal to sync with Google Calendar and save myself the $99/year. I could even use this method to sync my handful of Macs I use on a daily basis that are now tied together with MobileMe, and use the browser-based tools on my netbook and when I’m away from my machines. The only two things I would lose by moving to Google for all of this junk is bookmark syncing and iDisk - but with services like Dropbox, the loss iDisk would be no big deal. And I can live without bookmark syncing

There’s one thing keeping me from an all-Google fix: If you have an Exchange account setup on an iPhone, it disables USB syncing for data.

Yes, really. This means that I couldn’t sync locally with my machine. A nd there can only be one Exchange account at a time on the iPhone, so even a service like NuevaSync  isn’t going to help me.

Effectively, since we use Exchange at work, I have to use MobileMe for syncing any personal data with my iPhone. So for now, I’m syncing my contacts with MobileMe to get them on my iPhone, and with Google to get them in Gmail. iCal just syncs with MobileMe - I can get to my events at me.com if needed.

Looks like I’ll be forking over another $99 when my MobileMe subscription expires in 2 weeks.