It really depends on the weight that you are putting on the tires. If you have a tire rated at 2033 lbs per tire, on a estimated 4000lb vehicle, then max inflation is probably going to be a little overkill. I would definately not recommend running at max PSI in the front, you will affect the handling and steering of the vehicle. (i.e. wandering, twitchy steering, etc.)
Although it's a bit of a pain, you could always do the chalk test. Take a big piece of white chalk (kids sidewalk chalk works well) and make a thick line across the tread face of the tire, outside to inside. Drive 30 or 40 feet and check the line. If it's all evenly rubbed off, you're good. If the outside edges of the line are gone, but the center is still there, you are under inflated. If the opposite is true, you are over inflated.
That is method Jeepers use to judge proper inflation when going to larger-than-stock tires. My Jeep has 33x12.5x15 tires on 15x10 rims, and I run 26lbs in each to keep the tread flat on the road. My tires are load range C, 2550lbs at 50 psi, but my 3,800lb Jeep doesn't need anywhere near that much load capacity, and really gets squirrely at higher psi.
When towing with my Expedition, I run the fronts at 33psi and the rears at 38psi, factory says 32 and 35. The handling gets really bad if I go up any more in the front. If you are running factory stock size tires, you are usually fine running whatever it says on the door jamb sticker or your owners manual for the front tires, and maybe add a couple of psi in the rear when towing. Like egMike said, the boat probably only adds about 200-300lbs (usually 10% of gross trailer weight) on rear of the vehicle, everthing else is carried by the trailer. Your engine, tranny, and brakes are going to be abused more than the tires.
Sorry to blather on, I'm bored at work, and this topic comes up once a week on the Jeep boards.