I got curious and did some approximate calculations for my boat on my trailer using the picture i posted as a reference for distances from hull cradles and such and with minimal assumptions, I figured that my boat sees a shear loading of approximately 75lbs and a bending moment of 302lb*ft at the back of the rear hull cradle. That’s about the same as pushing on the bows with 37lb while the boat is on the trailer.

Although this work didn't really lead to any useful answer or information for the problem of cyclic loading on a catamaran trailered backward w/ 8ft of cantilevered of bow. Or give me an idea of loads when the trailer goes over a bump, I still found it interesting (as an engineering student) and got to actually make use of statics class. Who da thunk it.

I am not sure that I agree totally (because of lack of evidence) that tralering this way will cause my bows to weaken. It could very well be that catamarans break at this location because it has the potential to see higher that allowable loads when sailing on the edge. But I may consider finding a way to slide my boat a foot or so forward on the trailer anyway to ease my mind now.

I prefer to remove my rudders b/c I am a poor college student w/ carbon rudders and I like them a lot.

Oh, and I do have a red flag. See first picture attached. Now thats just common sense.

I attached some of my calculations for those interested. I really spent way too much time thinking about it but i'm an engineering nerd so whatever.