For instance . . .

The Google Calendar sync tool should support syncing Outlook to secondary Google Calendars, not just your primary calendar. That would mean I could drop SyncMyCal which runs in my Outlook-only Parallels Virtual Machine. I’d have a nifty, no-click workflow to sync my Work calendar to my secondary Work Google Calendar, which get sync’d down to iCal and to my iPhone.

Better yet . . .

The iPhone should support syncing both iCal and Outlook calendars. It’s sort of a dumb thing that if you turn on Outlook calendar and contact syncing, that’s the *only* calendars and contacts you get. Why not keep them separate? If Apple added the ability to have your Outlook calendar sit right along side your iCal calendars, then I wouldn’t even need to sync my Work calendar up. I could just accept meeting invites on my phone and have everything work nice and happy.

Oh, and same goes for Contacts. Just let me sync my Exchange contacts as a separate group. Seriously.

Even better . . .

Apple Mail and iCal should build in real Exchange support. Then I could actually not run Outlook in my virtual machine all day. Instead, I could just use Mail and iCal as Exchange clients and have the most simplified workflow of all. Supposedly, this is going to happen in Snow Leopard. That would be awesome.

Making life even sweeter . . .

Google should fix contact management. I love Gmail. I use it for everything. I hate Google’s Contact stuff. It is awful. They tried to make it better. It didn’t work very well. But they’ve got the keys right in their hands … Social Graph. Imagine you gave Google some information about you that they could use some OAuth or other authentication means to determine that it is really you. So you hand them some keys to Flickr and Twitter and (if they can work out their differences), Facebook. Now, Google pulls all that information together and makes a nifty contact for you. Name, picture, email address, home address, work address, phone number, Twitter, Flickr, etc, etc. You only get as much information as the contact allows (if we’re not friends on Facebook, you don’t get my phone # or address).

Now, Google can do all this behind the scenes and give you a little button to “add so-and-so” as a contact. If I add them, they go into my Contacts section. Then, I subscribe to my Google Contacts like they’re an LDAP source or however else they want to get hooked into your setup.

Boom. All of a sudden I’ve got a real contact solution that’s continually updated.

Ok, sure, that’s a lot like what Plaxo promises. Except Plaxo really doesn’t work all that well.

So. When all this happens, I’ll have my calendars all seamlessly syncing together to my computer and to my phone. On top of that, my contacts (work and personal) will all sync nicely as well. And stay up-to-date, thanks to something like Social Graph or the like. Plus, Snow Leopard will mean I don’t have to run a Virtual Machine just to use Outlook (and don’t tell me to use Entourage … it barely works).

With my work life (and personal contacts) working so seamlessly . . .

I’ve got time to kill. I want to get through some movies or TV while I’m out and about.

Give me Netflix Watch Instantly and Hulu on my iPhone! Now that they’re on my XBox and Mac, I’d love them remotely. When I’m out eating lunch or riding in a car, I don’t need HD video. I just need crappy streaming video that will let me knock off an old episode of Newsradio or watch 15 minutes of a crappy movie.

But, if I don’t want to watch something . . .

Sometimes I just want to listen. The fact that the new version of the iPhone firmware lets you download podcasts is great. By why doesn’t it sync my entire podcast list and let me just quickly scan for a new episode of something I listen to? Even better, why not do something similar to Genius and recommend me a podcast I might like?

All that would be very cool.

Oh, and why can’t I sync stuff over bluetooth. That would be good too.

It shouldn’t be that tough, but so far, it has proven elusive. I’ve tried some of the free tools that are around to sync iCal with Google Calendar and Outlook with Google Calendar, but they’ve all proved a bit wonky.

Finally, Scoble mentioned that Plaxo had it’s new beta that would do all of the syncing through a nifty web application. So, I headed over to Plaxo.com and tried it out. It seems pretty straight-forward. You add “sync points”, which are places that Plaxo will sync your data to. I added Google Calendar, my Mac, and my work Outlook. The latter two required the installation of some software. Nothing too difficult. A couple of config tweaks later and I saw my work calendar in my Google Calendar and sync’d down to my Mac.

Perfect!

Except, over the following few days, I would constantly get duplicate calendars, lose the original calendar, get duplicate entries, continually have to tell Outlook which calendars I really wanted, which it would ignore and keep syncing other ones.

It became a royal mess.

So, I decided to uninstall things, get back to square one, and at least retain my Google Calendar the way it was. Except Plaxo ate my two calendars (because they no longer existed in Outlook … lesson: kill your sync points before killing your calendars). That kinda pissed me off. Thankfully, my Mac still had my calendar, so I was able to dump the ICS entries and upload them to Google (import of ICS files is a nice feature of Google Calendar, by the way!). I lost my music calendar, but it was mostly older stuff at this point, so I started that one over.

Plaxo just didn’t work for me, though it seems like it could be useful if they work the kinks out. It didn’t sync to Google Calendar fast enough, which was always a bit annoying. The apps for the Mac and PC were kind of clunky, but they worked ok. But borking the calendar syncing was just a bit too much to deal with at this point.

So, I’m back to just subscribing to my Google Calendar feeds through iCal. I’m going to try gSync for about the 4th time and hope that the final release version is finally good enough to maybe think about using full time.

It’d be cool if Google solved this problem themselves (maybe opening up the GCal API), but I’m not holding my breath.