I would do the turbo first. Why? What if you had a gear ratio of 5.24:1? Would that help you maintain the hill speed? You'd think so, but no. Unless 50 is your desired speed to maintain.
At a weight originally of 6,100 lbs my hummer still lost speed up hills. Now with a factory gm6 and factory injectors both with 65-70,000 miles on them and half a turn on the db2 I accelerate up the same hills weighing over 9,000 lbs. and towing a small camp trailer.
I can not stress this enough- TURBO!