In my experience as a student, facilitator and coach of this information, the best labelers are the ones that are not attached to computer software.
Personally I don't want any excuse to get in the way of me filing. Excuses I've heard:
"I'm out of printer-ready stickers"
"I don't want to put a whole sheet of paper through the printer for one label"
"The server is down, I can't log on to my computer"
"My computer is off, I don't want to start it up to make a single label"
Our staff all use Brother labelers. The ones that plug into the wall (or take batteries, whichever the user prefers). Also, fyi, I have a monthly recurring reminder in my calendar that reads:
"Do I need to replace the label tape in the PTouch? This saves me from "running out" of tape when I'm in the middle of processing my in-basket!
I have the PT-1500 and love it. I use my computer all the time, and am not affected by the issues mentioned by Mr. Womack.
The printer comes with two programs: a super-duper label editor that can do anything (which I have seldom used) and a "quick" label editor. I have the Quick Editor launch automatically on system startup. Any time I need a label I switch to the program, type (or frequently paste), and hit print. All done.
The labeler itself it pretty good. Good quality labels. Easy to switch cartridges. I originally looked at the unit because it was cheaper than other PC labelers ... and it turned out to be the best choice for me.
If you are not a heavy computer user, then the hand-held unit is probably the better choice.
I have a Seiko labeller at work (attached to PC) and a Brother labeller at home. I would never get rid of the Brother labeller because its portable, and because I don't always have my PC on at home. However, I like the PC labeller so much, I plan on getting one for home. I frequently need to send packages, and I like a typeset label for those. But having both does prevent excuses (of which I have many). So, my suggestion would get both, but if money is an issue, start off with the Brother handheld.