Life isn't easy for a Mac user with a PocketPC. They just weren't made to work together, situation normal for Windows systems, I suppose. However, the situation isn't entirely hopeless.
There are two software packages on the market for the Mac designed to ease the connectivity issues with PocketPCs, namely The Missing Sync and PocketMac Pro. Read on for more information on how they stack up.
Both applications boast a similar feature set; iCal and Address book sychronization, integration with iPhoto and iTunes, the ability to share your Mac's internet connection with the PDA, etc. PocketMac goes a bit further and also offers sync with Entourage, NOW Contact, and Mail. And both allow for installing PocketPC applications onto the PDA. The PocketMac software currently includes an added bonus of a PocketPC Theme that when installed gives the PocketPC a look very similar to a Mac running OS X, which is a nice bonus.
So, how do they compare then? For basic synchronization with iCal and Address book, both apps did a good job, transferring data in about the same amount of time, both integrate with iSync for facilitating this. iPhoto and iTunes syncing involves adding a plugin to both apps to allow syncing, but again these functions seem very well thought out, and work well in both products.
For me, the big difference was noticed when trying to install applications onto the PocketPC. The PocketPC uses a file format called .CAB, similar to the Mac's .pkg file, it's a self contained format that includes everything needed for the app to run. If the app you want to install is available in a .CAB file, then you're usually in good shape on the Mac. Should you not see this format available where you download the software, check with the author to see if this file format is available, usually it is.
With the Missing Sync software, installing items was as simple as clicking the Install File button in the application, the file is automatically transferred to the PocketPC, and if additional installation is necessary, the PocketPC pops up a window walking you through the steps.
With the PocketMac software, a nice feature has been included that actually will look into a .exe file (the format most PocketPC software is distributed in) and will attempt to extract the .CAB files burried in the .exe. I say 'try to', because of about 6 different apps I tried this on, not one of these was able to be installed. To be fair, the application does caution that it may not work with all files, either I had incredibly bad luck, or this feature isn't quite ready for prime time just yet. Installing a straight .CAB file worked much better, but oddly these files took a very long time to transfer, much longer than it took for the Missing Sync software.
Now, let's take a look at the two companies. I initially contacted both companies about reviewing their software for my office, I received an almost immediate response from the folks at Mark/Space, makers of Missing Sync. In fact, I received the software even before my PocketPC arrived. I received absolutely no response from PocketMac, even after a second request was made for an evaluation copy. After some wheeling and dealing, I was able to procure a copy of PocketMac from a gentleman who was selling his PDA and including the PocketMac software, and it turned out the buyer wasn't a Mac guy, and he sent me the included CD at no cost. So, just to keep the record clear, both of these are official registered copies of the applications.
One thing that can really set apart one company over another is their support after the sale, assisting users in resolving their issues. The more complicated the software, the more important support should be in considering a purchase. Im the case of these two apps, I had minor problems that I needed assistance with once I had things up and running, so again both companies were contacted for assistance.
As before with Mark/Space, I received a quick answer to my issue, which turned out to be the need for a newer release of their software (I was having slow internet access when using the internet sharing feature), and that fixed me up nicely. With the PocketMac folks, my issue was in registering the software I'd gotten second hand in my name. Also as before, repeated contacts yielded absolutely no response. Almost a month later, I still have an open case with PocketMac that hasn't been updated by any of their support staff since the nice but unhelpful woman I spoke with on the phone entered the notes into their system.
So, all things considered, my own opinion is that the Missing Sync software wins this one hands down. It's a tightly integrated package, supported by what seem to be a great bunch of folks. With a retail price of $39.95 (Download version), it's money well spent.