The first device I recall trying to sync with my Windows PC was the Casio Cassiopeia, one of the first Windows CE devices to hit the market. Palm had already released the popular Pilot and Microsoft felt they had to get a piece of the action. I worked at Microsoft at the time and happened to be attending an event in New Orleans where the Cassiopeia was sold at a discounted price of $250. I couldn’t resist.
I spent hours attempting to get that bugger to sync with my PC. This was before USB was around so I was stuck with a serial port and it was a painful experience. Eventually I gave up and entered my contacts, tasks and appointments manually. So much for my handheld time saving device.
I eventually sold the the Cassiopeia on eBay and purchased my first MP3 Player; the Diamond Rio 300. It would be an understatement to say this is the worst couple hundred dollars I’ve ever spent. In theory, it held 8 to 10 songs. In reality it rejected everything I threw at at. The included software must have been written by an RIAA mole working at Diamond.
I’ve owned more than a dozen phones, mp3 players, Pocket PCs, Handsprings, Palm Pilots and all gave me problems connecting to my computer, syncing data or both. Although the iPod is known for it’s friendly design it’s not perfect and I want to toss it into the street at least once a week. Some days it won’t connect to iTunes until I reset it.
I currently have two phones with Windows Mobile which is the equivalent of asking a complete stranger to kick me in the head twice a day. Both phones are molasses slow and occasionally connect to Vista. Unless they decide not to which lately is quite often. My phone is setup to sync my email with Microsoft Exchange and it does work most of the time, but it doesn’t like to connect to my PC without a number reboots.
I’m tired of all this connecting, syncing, and partnering which leads to lots of rebooting, resetting, unplugging and swearing. It’s been over 10 years since I purchased my Cassiopeia, yet syncing problems persist. One would think that USB and Bluetooth would make connecting and syncing devices much easier, but many problem still persist.