Used to do the commute from Wicklow Town (from their originally). Service itself always plays second fiddle to darts, so you are looking at 1 hour 20 minutes there or there abouts up and then same back. Problem is, you are at the lap of the leaves, takes little to cause a delay and then you could be racing to work. Bus service form Wicklow is very good, but again you are looking at hour and half into town.
In saying that, I love the town and their is a great community down there with a lot happening.
Second what Dereko1969 says, Taxsaver ticket is a must if available through employer. The problem with the difference in Greystone and Wicklow is you will spend a lot more on a house in Greystones.
Kilmacanogue has the 145 Dublin Bus Service from it and the 133 Wicklow bus (which goes to airport), and stunning views in the surrounding area. Asford is a lovely little village, but you are not far from Wicklow so the difference in time saving is minimal.
Alternatively, you could drive up and get the luas in daily.