Railroad - I would be worried about something hitting the props, especially if crossing dikes, logs, or levees. When the transom drops off the ledge, the turning prop could hit as the boat slides into the water. It would also push the rudders further back.
About a decade to two ago, there were lots of single rudders that looked like cross-sections of airplane wings. One of the biggest reasons I heard they got away from them was that they would hit levees while crossing them.
Also when running in deeper water and you let off the gas quickly, your wake will catch up and sometimes spill over the transom. With the prop behind the transom, you would have the prop regularly hitting the water and that is not a good situation. Several good prop strikes into water with a wooden prop and it can start having some dangerous issues. Composites are stronger, but hitting water is still much more stress than what they are designed for. I would be scared of scattering a blade.