Tari S. says most of the points that I would say with a few differences. First, a bob is actually one of the hardest cuts for a stylist - it has to be so exact and works best on certain types of hair. The other thing I would say is that while price doesn't/shouldn't matter it often does only because those stylists who are really good are that good because they have taken their craft more seriously and continue to improve through education and have a lot of experience to back them up and thus, will want to make a better living doing so. Also, really great stylists book up quickly and by raising their prices, they are able to more effectively schedule with a "regular" clientele. I actually go to a guy who cuts my hair and his partner is the guy who colors my hair (neither of them do the other work, i.e, the guy who cuts doesn't color and the guy who colors doesn't cut), they have their own specialty. This means they can charge more. With that said, I still only pay $60 for my haircut (plus tip so $72) and $95 for my "color" (actually bleach foil highlights) (plus tip so about $115). When my hair was short (a modified bob), I went every 6 weeks, now that I'm growing it out, I go every 8 weeks. Both of my guys are so busy that they are booked 3 months in advance, and I book my entire year of appointments with them.
I found my hairstylist at an Aveda Concept salon and simply liked what his profile had to say. The guy I went to before him was a fancy salon, but we just weren't clicking. My current hairstylist liked to work on short hair, and we clicked - we spoke similar "language" when it came to describing my needs. I think that is very important when looking for someone. While there is some truth to "you get what you pay for" there are also plenty of stylists who can charge a lot but not be the right person for you and there are plenty who are great, but haven't realized their full potential yet and are therefore still not charging a lot.
Good luck!
S.