I was looking at how my TheMightyHobie18 is positioned on my trailer. I tow it bows first and I still have my hulls cantilevered forward of the front crossbeam. My forward hull cradles are under the front crossbeam. It towing it stern first is a concern due to the moment loading of the cantilevered bows, I wouldn't worry about it. That's the lightest part of the boat and will see much more loading when sailing as the forestay bridle imparts it's load to the bows.

Nice real world application of statics, btw. If you do any design work in your career you will be be using it in the future. Keep that textbook. And Strength of materials and dynamics.