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I've had an Irrigation Caddy (wired, not wireless version) lying around for a couple of years waiting to be installed at our cabin. I finally got around to it this week, and I'm already regretting it.
Initial installation went fine. Interface is cludgy and very outdated. Seeing there were a number of firmware updates, I selected the latest one and followed their instructions for updating. Even the firmware update process reminded me of how things used to be in the 90s, not how they should be in 2015.
First, you have to download the firmware file yourself. You also have to download a Windows-based firmware updater. OK, that's a little old-school, but still fine. I can manage that.
The update process is also a bit old-school. You have to unplug the system, press a button in the updater program to "capture" the device, turn on the system, hope it finds it (mine did), then run the update.
My updated reported that it worked... but from that point, the unit was a brick. I never saw it on my network again. I tried the hard reset option a few times, but I could tell this wasn't the unit I wanted. And to add insult to injury, I've read that you have to pay $3.99 if you want a mobile app.
Unplugged it, went to Home Depot, and picked up a Rachio Iro. I plan on using it out here at our cabin, so I can compare it to the Rain Machine units I use back at the main house.
But run.... run away from the Irrigation Caddy.