Good catch, Blake! A quick mileage comparison of the route we did, only beginning with the Weeping Wall/Haystack Creek ascent to the Highline Trail only adds maybe a mile. The first almost 1000' bit from the Weeping Wall parking lot up to the Highline Trail, is of course a grunt, but a relatively short distance. What you suggest is definitely a viable alternativeguess it depends on what climbing views you wish to deal with: a winner no matter what!
The climber's trail is in my opinion a much more scenic route both ways. That trail from the Loop seems to last forever. I would much rather walk an extra mile and have less elevation gain.