For me its an issue of comfort vs. durability. Price isn't so much an issue as a more durable boot will more than justify its higher price tag within reason. I've worn out so many pairs of $150 dollar boots in a matter of months that spending $300 or so really doesn't bother me all that much if I get more than a year or two out of them. Especially if they have a decent warranty which many boots in that price range do.
The comfortable boots I prefer as I said are Keen's but I'm on my 5th pair and these super comfortable boots just don't seem to be lasting like they used to. The foamy type rubber on the sides of the sole is just disintegrating off a pair of boots I started wearing two or three months ago. ...They're made in China.
Talking to close friends who work on professional trail crews in national parks such as Yosemite and the Adirondacks and all over the country and the world the consensus is that the only decent boots that stand up to the abuse that that type of work brings are made in Italy or Romania. (brands like Asolo and La Sportiva) These guys and gals are some of the only folks I know who are tougher on boots than I am going day after day for months in back country doing rock work and hiking hundred pound packs into remote places everyday in all sorts of weather and terrain. They beat boots up and don't take kindly to blisters, wet feet or getting trench foot. Now what they do is a pretty damn good test for boots for our kind of work (which is hopefully a little bit lighter that what they're doing) so I've really taken their word for it. If you want boots that will last, and offer you good protection, you're going to want something thats almost fully leather. Leather boots with gore tex are awesome.
Also, its extremely important to treat your boots. I use saddle soap, snow seal and or some kind of natural leather dressing. I'm currently using Red Wing's dressing which is Pine Pitch, Mink Oil & Beeswax and works fantastic to keep leather protected, waterproof and looking like new. You'll get more life out of your boots this way, you really need to treat them.
While I have some Keen's and Merrell's I'll still use lightly, I had to find something a bit more heavy duty for the coming season to help me from going through two pairs of boots. At first I picked up a pair of LL Bean Cresta's. A full leather boot made in Romania, Goretex. A real awesome hand crafted old school boot. Unfortunately that night I took it for a 5 mile hike and by the end of it my feet were killing, beyond what you'd expect from breaking in a new pair of boots. The soles were just too narrow for my feet. I'm very thankful for LL Beans awesome return policy. They're a great company. I returned them the next evening and picked up a pair of Asolos from EMS. And I love these things. I'd recommend anyone to try out the Crestas as they're a well made boot, $240, and I've got a good friend who is rough on boots (we hike together often and sometimes work together) and he has 3 hard years on his Cresta's and they're still going strong.
The Asolo's I picked up at EMS later that night are great. They're a bit stiff as I expected but very solid boots. I have two other close friends who are each on year 3 on their Asolos. One is a landscaper/tree climber, and the other a trail crew worker who is currently rocking his Asolos through the jungles of Belize and they both love them and their boots show minimal wear for the abuse they have dealt with. The pair I picked up was $295. The link is below. I know a few other people with these boots who love them, so I'd say they're definitely worth checking out. Be warned both these boots are stiff at first, which should be expected from a tough made boot. My Keen's are like walking around with marshmallows strapped to my feet, but unfortunately they also have the durability of marshmallows.
Take care of your feet guys! Your back and knees will thank you!
Hope for those of you that took time to read my boot rant, that it was helpful!