I've been asked this a few times so I am writing this up as a post.

A while ago I was elated when I took a chance on Elinchrom Skyports in lieu of the expense of Pocket Wizards. I loved them. Then, only four months later people saw that I was using Pocket Wizards. That didn't seem to make sense. Didn't I profess my undying love for these sensible, affordable radio triggers?

Advantage Skyport:
Yes, I did. The Skyports are still a great product in my book.

-- they are small, you can fit a whole set in a big pocket and they don't poke up half a foot above your camera
-- they cost significantly less than Pocket Wizards
-- they are made by Elinchrom, a reputable Swiss manufacturer
-- they have multiple channels. Six compared to Pocket Wizard Pluses (the model I went to) that have four channels.
-- they come with a number of different sync cables

and more importantly:
-- they trigger flawlessly. Every time I squeezed off a frame on my Canon 30D, the Skyport transmitter on the hotshoe made every other trigger connected to another strobe fire. Every time.

Why did I do it?
So then, why did I sell mine off and spend another $200 above what I got from the Skyport sale to get the same number of triggers that I needed (1 transmitter + 3 triggers)?

The answer is: everyone at the Strobist meets was using Pocket Wizards.

It is a cruel, cruel world when you are different, no worse technically, but outnumbered and, more importantly, incompatible with other players. My Skyports worked very well in my setup but every time I wanted to shoot on someone else's setup, I had to borrow someone else's trigger. And anyone who wanted to shoot on my setup had to borrow my Skyport transmitter.

That is what it was like for me the first big meet. Sure, I was rocking my setup, one of five that got in the rotation that day, but I also felt a little isolated. Meanwhile, all the other photogs merely floated from setup to setup, changing channels.

Working by yourself? Make your choice
I felt better when I was back home in my home studio. There it didn't matter that I was alone in a sea of Pocket Wizards. My own work is my own universe. I could still be using the eBay Triggers (that is, if they didn't suck) if I never went out to work with other photographers.

And that, for me, is the key. I wanted to work with other photographers and, unfortunately for Elinchrom, Pocket Wizards are the industry standard.

Now that I've used both Skyports and PWs, I can say I really don't prefer one over another for any technical reason. PWs advantages over Skyports are not that much for what I do.

Advantage Pocket Wizard*
Pocket Wizards:
-- have much longer range than Skyports. But then I don't do much that needs that.
-- are transceivers. i.e. they are both transmitters and receivers. So you can take any out of your bag and pop it onto your camera or onto your flash. That is pretty convenient when you have to set up quickly. With Skyports you have to get a transmitter and then get a cloud of receivers.
-- can be locked onto the hotshoe. For some retarded reason, the Skyport transmitter is held onto the camera hotshoe by friction alone. So you can brush it off your camera.
-- take AA batteries whereas the Skyport receivers have their own rechargeable internal battery and must be charged in a wall socket. So if your PW receiver starts acting up, you can just swap the battery with AAs you can buy at any corner store. Skyports, you have to make sure to recharge before your job. In truth, I never had a problem with that. In four months I recharged my receivers maybe three times shooting every third day.

The Mac vs PC thing
This could be another Mac vs PC thing. You could, for example, start working with a group who are mostly Skyports. In that case, you might be thinking about swapping PWs for Skyports.

-or-

You could be agnostic and keep rocking those Skyports but buy one PW just so you can work with others (on their setups). One part of me wishes I had done just that -- but then it would have taken me much longer to build up my PW collection.

Final note. After I got my PWs one of the local photogs chose Skyports. Could this start .. a new trend? Maybe I abandoned them too soon? Maybe maybe...?

Cue suspenseful music...

*Note: I am speaking of the Pocket Wizard Plus II