Trivial may be the wrong word. It's easy if you fill all the requirements. In SF we had an LLC, an apartment in the mission, a lawyer to fill out the paperwork, and 8 Canadians. The canadians all did have college degrees. I honestly don't know if the border patrol even checks all of this stuff. One of the guys said it took about 20 minutes to get through. It probably depends on what border you go through. In my experience the small borders are the worst, because the border patrol are from small towns and have nothing better to do other than fuck around with you. (this is also assuming you are driving) The best driving border is BC => Washington. Flying in, the west coast seems the best.

On the other hand, I know loads of people who go from Europe, Japan and Australia to California, NYC and Hawaii simply to hang out for 3 months at a time. These are people who have no college degree or any useful skills at all. They are here to surf, snowboard, or loaf around new york. Getting into the country is not a huge problem. The threads on this topic often have a tone of excessive worrying about visas. You can easily show up in the country and hang out for a while.