The problem, is on my livingston I cant get to the front of the transom to use a bolt, anyone have any ideas? Dont want to cut an access hole on each side, is there any way to screw them, or maybe some sort of expanding anchor thing?
There is a probably better ways to do this. Drilling holes into the boat to mount wheels would not be very wise, especially if you cant get them out of the way. I suggest make a small, rigid dolly out of PVC Pipe. You would be amazed how much it would hold. Making it to cradle the boat hull would allow it to do exactly what you want with the wheels. Slip the boat off and lock it up near by where you launch at.
One of the best lessons I learned from my dear Grandfather was "If you have enough money you can make Niagara Falls run backwards." You are going to have to run lights for the boat as well. Where ever you choose to mount these flip up wheels the stress from the weight plus an engine on the wheels will most likely, no, will compromise the hull integrity. A proper trailer distributes weight, 2 wheels don't. My advice to you also is don't do it or get a tin boat. Just throw it on the roof and go.
I can't get my head around how you move a glass boat that heavy without a trailer.
Still sounds like making a cradle would be you absolute best option. Check out some cradle builds for kayaks... same principle, just increase the dimensions.
Have you tried to drag and push the boat around yet? What kind of weight are we talking here? The other thing I must ask is that boat going to be in exact same spot for the season? That I see as doable with a small dolly not wheels on it. My brother has a 14 foot tinny at his lakeside cottage and he drags the boat up on the lawn at the end of a day. He uses 6" ABS pipe as rollers under it. It is on relatively flat and smooth ground. With all the add ons he has put in her plus the 25 HP 4 stroke, electric bow mount, gas etc. it's actually far too heavy for 2 older guys to lift easily. The older I get the stronger the Earth's gravitational pull. I do have a wheel idea but it is a bit complicated to explain without drawings etc. Basically a cross tower/axle across the stern that locks in the up and down position. Mounted above the waterline on each side. A small dolly would be less expensive less complicated and not compromise the hull. All that time reinventing the wheel can be spent on the water.