Multiple Computers? Synchronize them!

Many of us now have a computer at work and a computer or two at home, and a cell phone or a PDA, and we want our schedule and files to be available on all of them. Over the last year, many new file synchronizers have been released by companies, most prominently Apple's release of Mobile Me – they say they got it right this time. Did they? How does it compare?

I've tried to find a way to synchronize my files, my calendar, and my bookmarks across three computers, a cell phone, and a PDA. I have a Mac, a work PC, a home PC, a Palm Treo, and a iPod Touch. The quest is to see if we can get all or most of them synchronized – without risking loss of privacy (for example, if you want to make sure your personal calendar is stored somewhere your boss can't see it).

Bookmarks
Compared: MobileMe, Foxmarks
MobileMe only works if you use only Safari on your mac. On Windows it supports only Safari or Internet Explorer. For me, Safari was almost good enough but Firefox has a more refined bookmark manager and I found it easier to deal with my 2200+ bookmarks on Firefox – Safari with that number of bookmarks is very clunky. Firefox is not an option with MobileMe. Safari is not an option for Foxmarks.
Winner: No overall winer. Use Foxmarks if you only use Firefox, and use MobileMe if you only use Safari and an iPhone or iPod Touch.

Calendar
Compared: MobileMe, Plaxo, CompanionLink, Google Calendar Sync
MobileMe is the easiest to set up, but can be too easy – it treats all information the same way, which can be a problem for privacy if you want to keep some calendars off your work machine. I want to get my work calendar on my cell phone, but I don't want to put my personal private appointments on my company's public Microsoft Exchange server – I don't want the IT guy to know I went on a date with my girlfriend last night and that I have an eye doctor appointment on Thursday. For this, MobileMe would not work, and neither would Google's Calendar sync (which also doesn't support mac). CompanionLink almost works – it syncs with Google Calendar and it'll sync only with the Calendars you want to sync, but it is buggy (it kept putting duplicates of events up on Google Calendar which I'd need to keep deleting) and you need to buy a new copy for each computer you get – that can get pricy fast. And, it doesn't work on a mac – Windows only. So, CompanionLink is out. Next, I tried Plaxo – a little harder to find, but free across computers, and it syncs whatever calendars you want with any other calendars on iCal, Outlook, Plaxo, Google Calendar, and more. I was quite surprised! I ran into a few bugs, but less bugs than other systems and I managed to fix it and clean up my calendar. So I can accept an event at work in Outlook, a personal event in Gmail (though sometimes it fails to sync with Google calendar for an unknown reason), and they both show up on my Palm Treo – exactly what I was looking for.
One thing to remember – if you start synching your calendar with multiple computers, you start having to worry about whether your computers had time to sync with each other while they were online – if they didn't get time to synch up, one calendar can still be out of date behind other calendars, and the longer the chain of computers, the more likely something will be out of sync.
Winner: Plaxo

Files
Compared: MobileMe, Windows Live FolderShare, Unison, PowerFolder
MobileMe almost worked. It was easy to set up, but I had trouble getting mounting the files under it to work under Windows – this is probably a Windows problem. Also, it seemed to think that there were sync errors when there were none – sometimes when I turn on my Mac it makes me go through a list of a hundred items to tell it that none of them have changed.
Windows Live FolderShare was easier to set up than Mobile Me on both my Mac and Windows machine. The strength and weakness of it is that it doesn't store your files on a server, it just sends them back and forth between the two machines.
Unison is an oldie. If you're a technical user and willing to spend hours writing config files and setting everythng up, it might work. But if you have machines behind firewalls or routers, you might never get it working. Plus, the UI is depressingly simple comand line system.
PowerFolder was fairly quick to set up, although it has a fairly complicated front end (my girlfriend needed help setting it up for her and had trouble understanding when it was working and when it wasn't working). PowerFolder does a mediocre job of abstracting away the need to understand your network. However, it uses an online backup solution – Windows Live FolderShare does not have an online backup. The online backup solution worked from all of the computers I tried, and after configuration I had few problems with it.
Winner: PowerFolder


Summary
So, there is no one solution that will solve all of your multiple computer woes with no fuss – at least not yet. However, you can put together a series of tools to get the magic to happen in the background – once you put them all together and configure them all, the magic will happen in the background.