So much for simplification (geekery)
So I guess I'm still using the Palm, at least as a conduit to sync between Outlook and my Mac at home. I'll just have to have the Mac put all my appointments on the phone, and hope that any appointments scheduled on the same day as the event have the reminder show up when I'm at my computer at work (since I've set the Palm's alarm to be silent since I was just hoping to reduce the number of alarm-raising devices). Oh well. I was still keeping the Palm in my backpack as a quick-access web device anyway, so this way I can still just keep it in my backpack instead of needing to put it in my pocket. Which still solves the primary problem of "too much crap in my pockets."
Fortunately, since the last Palm sync was with Outlook and not my Mac (post migration), the Palm didn't have any weird conflict issues when switching back. I was worried it'd totally mess up my Outlook calendar.
The problem of synchronizing multiple devices with multiple computers shouldn't be that hard to deal with. Unfortunately, none of the devices support a reasonable subset of each other's data; recurring appointments are the most problematic (although the phone supports basic recurring tasks, all the sync conduits for it, including iSync, just put individual instances of each appointment on the phone since the other PDAs' support is so much more robust) but then there's also issues with addresses and phone numbers (the phone doesn't store addresses), and records don't maintain any sort of GUID or other stable recoverable mapping between the two devices. Also the phone reformats its numbers to be a nice standard format, which is great from a consistency POV but pretty blecky when the sync conduit assumes that (800)555-1212 (how Outlook formats it) and 8005551212 (how the phone formats it) are different numbers and so then I end up with duplicate entries for a lot of numbers.
But yeah, ANY sort of GUID thing (even if it's a device-specific thing) would be very nice, because then each sync conduit could match up external and internal GUIDs and maintain a stable mapping. There'd still be issues with deletion and so on (how long to persist a record which indicates that a GUID was deleted, for example) but at least you wouldn't have to worry about records being modified strangely.
Even iSync gets this wrong, though. If you have one phone and two Macs which sync via the phone it works fine, but then if you get a .Mac account and sync the two Macs with each other and with the phone, things break really badly (every time you sync the computer which wasn't the one which last synced with the phone, it imports all of the phone's records). Or at least it does that on Ericsson phones and Palms.
It's just kind of frustrating, because let's say you have two Macs (a desktop and a laptop), a .Mac account, and a Bluetooth cellphone. You normally work on the desktop at home, so you normally sync the phone with the desktop. But then you go on the road and someone beams you their business card via infrared or you enter it into your phonebook or even enter it on the laptop's address book or WHATEVER, and you want it to be in both your phone and the laptop right away. So you sync the phone and laptop. Then it gets replicated to the desktop at home (via .Mac), then you get home and sync again, and then it imports another instance of the card from the cellphone.
Or, take my current situation: you have two computers (a Mac at home and a Windows system at work) and two devices to keep in sync (a phone and a Palm). The two computers can only sync via one of the devices (even if there were .Mac or some other iSync conduit for Windows, .Mac is too expensive and/or the company's security policy forbids that sort of thing, rightfully so). So you have to choose one device to be a conduit between the two computers, and have only one computer sync with the other device. But say you want the phone to be used for all appointment reminders, and of course the phone should have all the phone numbers in it. So the only way to keep all devices in sync is to sync both devices at home and only one at work, meaning one device will be lagged.
Another big nuisance is how there's no way for an appointment to specify which devices a notification should be sent on. So now, any time I have an appointment, three alarms go off - Outlook, iCal, and my phone. (Actually, four do, but the Palm's alarm is turned off so I don't notice the fourth one.) I used to mitigate this by having my phone only get 'home' appointments and my Palm getting only 'work' appointments, but then that meant needing to keep the Palm with me at all times, and of course this also made it harder to tell whether my Palm or my phone was going off since vibrate feels the same from both of them.
But if I'm feeling this much scheduling overload just as an SDE with two meetings a day (on average), I can't imagine how difficult it'd be for my manager whose schedule is usually packed and in constant flux. But I think he doesn't even bother with any sort of syncing; he just uses his work laptop for everything. No idea how he handles non-work scheduled stuff though. Maybe he just doesn't do anything outside of work to begin with.
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