I expect at worst the same range loss than I get with my Toyota Sequoia towing almost 8,000 lbs, and that's less than 30% loss. Still plenty to get from one supercharger to the next (this has been discussed in other forums).
- - - Updated - - -
One more note. I think there are a couple unknowns that should only make the range loss smaller.
1) towing a trailer on the highway is primarily a drag (wind resistence) problem, my sequoia and trailer are pretty bad when it comes to wind resistence, so I would focus on a more effecient design for the trailer
2) regen from a trailer 'pushing' the Model X when slowing (not braking) might be pretty significant, effectively getting back some of the energy used to get the trailer going. This might be nothing, but it might help a bit.