The worst pack-out I have done was one that a friend from the state we were hunting was in on. He was an outfitter for 25 years before selling his business. He told my buddy to shoot the bull they found, and he did, but neither knew the canyon they shot the bull across was a box canyon. None of us knew everything about where we decided to hunt that year. We packed the bull up and down through several side canyons before getting to a place we could cross the main canyon and get it to a place we could cut across to a horse trail and down. I had got my bull out the day before (with horses) and was on call for packing that day. Horses wouldn't have helped much on this one. By the time we reached the horse trail we were only a couple miles from the trail head. The resident called a few people to tell them where we were after we learned exactly what we were in for so that if things went wrong people knew where we were. The canyon was really loose walled and treacherous for footing. We got it done and the former outfitter said it was in the top 5 of worst pack-outs he had done. I had packed a couple trekking poles in when I met up with them with pack frames, and we cut a sapling to make a third. That pack-out wasn't possible without 3 points of contact on the ground at most times.
Honestly I don't regret a minute of it today. It definitely was a trial at the time, but it helped me gain confidence in what can be done with the right mind-set. We have killed a lot of late rifle season bulls in places they are late in rifle season because most humans aren't dumb enough to bother them there. Put one on the ground, put one foot in front of the other getting them out, and the pain ends eventually. Most of us are capable of more than we think we are.
Having a more experienced person along that time taught me a lot that has helped me be smarter in a lot of ways in years since.
I shot my best bull that year, a old 338" 6x6 with short tines but lots of mass and width. It was 7.5 miles from where we parked at the trailhead, but in a place accessible by horses with a little work. I had contacts made ahead of time for horse packing and I got my bull out with the packer while my buddy continued hunting. Just figured that was worth mentioning both because sometimes there is an easier way and because sometimes using outside help to get a bull out can help the guy who still has a tag make the best use of their hunting time. I know the money I gave the packer was well spent that year. I got my bull out without quarters going on frames and had a great time and learned a ton riding in with the packer and seeing how that whole process works. I have spend a lot of my life horseback on the ranch, but that is an aspect of hunting and horsemanship I had not been exposed to before. The education I got was well worth more than I spent.
As long as I am physically capable of packing a hind quarter out on my back I won't ever let the difficulty of the pack-out keep me from shooting a bull I want to harvest. That said, I don't feel the need to prove how tough I am anymore and will get him out the quickest and easiest way possible. I always hunt with the same friend and time we spend on packing my animal out is time taken away from his hunt or vise versa. We are definitely willing to do it for each other when the situation calls for it, but we are also both there to hunt. Good hunting buddies are hard to find partially because of things like this, I'm fortunate to have one that I have hunted with since we were both in middle school and continue to hunt with.