Backwards Trailering for Easier Mast Raising/Lowering???

I am wondering if it would be easier to tow my Getaway backwards on the trailer (stern first) so that I could use the rear of my towing vehicle (camper shell) to slide the mast on to for hoisting the mast upward (and/or even using the exisiting trailer-mounted mast crutch) for easier mast-raising and lowering...? In the past I have seen a few older Hobies towed this way, so maybe they did this for easier mast-raising/lowering.

Any thoughts or concerns? (Obviously the mastBob would need to be uninstalled while trailering since the mast top, not base, would now be the leading end up above the vehicle and straight into the wind while towing... but I've been leaving it off while towing anyways.)

Thanks much!

Scott