I should start off by saying that I may be a lttle spoiled -- 2 years ago I paid $175.00 a pair or Terra work boots and they were the best boots I've ever owned. This time around I was trying to save a little money and I didn't think that there would be that much of a difference between the $175.00 Terra boots and the $100 Timberlands. Unfortunately I was wrong.
The Timberland Pro Pitboss boots seem like a good pair of boots for someone who only needs to wear them occasionally.  They appear to be well made and they've held up well after two months of use, but for everyday use they're a bit heavy and bulky. They'll get me by for now but I've already started saving up to go back to the Terras.