Return on investment can be a bit of a tightrope act for some small and midsize businesses (SMBs). The business case for Kleine's upgrade approach didn't involve much in the way of circus tricks. "For us, it was very easy because we took that long-term approach. We did the timing correctly," he said. "By the numbers, we probably should have replaced all of this equipment a year ago -- so we got an extra year of value out of those other machines. As far as return on investment, it's really replacement investment because of that timing [and] the way we planned it out."

Kleine isn't diving blind into the Windows 8 waters; he has been using it on his own machine since early preview versions were available. "We [tested] our entire [software] suite on Windows 8," he said. "We were paying great attention to the beta." Testing has produced plenty of application compatibility issues with Windows 8, but Kleine said the OS has done a good job of identifying and helping to resolve those problems in largely automated fashion. "It has been more events, but the machine has taken care of it for us," Kleine said.

The single, integrated tech refresh will also help Kleine clear a key Windows 8 hurdle: User training. Microsoft's new "modern UI" need to be planned for in a corporate deployment.

"My adaptation is to teach people that [the] Windows key is their friend and make sure that they know how to tap that once to get the old style, and once to get the new style," Kleine said. "[Windows 8] is not something you just lay out in front of [users]. You do need to spend five to 10 minutes going through some of the keystrokes and the mouse positions to train that new user interface. I will say that everyone we have pushed in that direction has [eventually] liked it better than the XP or Windows 7 model, but it is change."

To ease the pains associated with such change, Kleine started with smaller Windows 8 installations with key staff to get them comfortable with the new OS. Those employees will ultimately help evangelize and train other folks as the deployment widens. "I always liken it to putting your toes in the water," Kleine said.

Touchscreen capabilities are on Kleine's radar, but not really for PC users. Rather, the next phase of the IT upgrade involves rolling out Windows Phone 8 devices to employees in the tree crews. They'll use their smartphones primarily for entering timesheets and productivity.

Tablets, on the other hand, are not a big part of McCoy hardware portfolio -- Windows-based or otherwise. "It's probably going to be desktops [and] laptops," Kleine said. "For our environment -- outdoors and high sun -- tablets don't tend to work too well. We tend to have contrast issues."

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