Greg, I agree that if it has the same effective wheelbase as the tractor, it will have the same ramp breakover angle, and with zero rear overhang (tow pivot at centerline of tractor axle) much the same risk of bottoming in the center of the wheelbase as the tractor has. However the effective wheelbase must be measured from the center of the ride-on axle to the center of the trailer's axle, rather than the way you've shown it in the sketch. The offset boom increases the effective wheelbase of the trailer - it's a simple Pythagoras calculation.
In my opinion what you have now is a better design, but I believe you still need an easy, convenient way to bring the trailer axially in line with the tractor, so you can go through gates. That can still be done - say, with a square-inside-a-square sliding boom and a vertical locking pin - but it may add slightly to the cost and weight. You have reduced the need for nose wheels on the trailer's cutting deck to the same level as for the tractor, but I think you still need an easy way to park the trailer without the front of the deck resting on the dirt and getting muddy and rusty.
It's looking better and better, Greg, but if you really go for the remote electric starting and declutching, with a separate battery and electricals for the trailer, I think it will become rather expensive, and rather heavy. Can you sell them for the price you would have to charge?
