Update:
I went out yesterday and ran it off and on (more on) for about 3 1/2 hours, about the same amount of time last go around. The tank was down to almost half and tank and bam, the problem started once again. At first it would idle for a few seconds, but got worse as it time went on. The engine was never hot, it never got above 170, so I don't think vapor lock has anything to do with it. I tried to wait it out and started it multiple times with no avail. Temperature even cooled down to 150, nothing. Then the weird thing is this; my buddy tows us to the dock and we start winching it up. The more of an angle the boat sits on, the better the boat responds to starting. Once the boat was at a 45 degree angle (steep ramp), it started and idled like nothing ever happened. I don't know if trash is pulling up and then settling in the tank or what. I bounced around the idea that the thing is out of gas and the gas gauge is not working, but after the last incident it only took 8 gallons. It's like clockwork, at the same time or rather when the same amount of gas in the tank it won't run unless at an angle. Wish I had more time to diagnose it, I'll have to wait for next week.
It's 106 miles to Chicago, we have a full tank of gas, half a pack of cigarettes, its dark, and we're wearing sunglasses.....................Hit it!