I agree with all that has been said. I've done it in the past and I would say my "maturity" has tempered by "Shoot now, worry about extraction later" tendencies.
There are places where public land bulls accumulate after the first surge of hunting pressure that are far from roads or have such topography that a smart guy doesn't even glass those locations. Have access to pack animals, tons of time and enthusiasm, or hunt in other places. Since I still want to hunt these kind of places and I have the time, though lack the enthusiasm, it comes down to pack animals for me; llamas.
This week we spent three days hunting a highly pressured unit in Montana; me, Beau Baty (llama guy), Matt Seidel from onX, Corey Jacobsen, and Donnie Drake. Each day was 10-13 mile loops into some really ugly places. Up early and back to camp 3+ hours after the end of shooting light. Just where the elk are in Montana general units by the second week of season.
Day One we saw 15 bulls. Beau shot an elk, the best elk we saw on the hunt. Thank God for his llamas. The next morning he and the llamas were on the trail to where we had left his bull hanging in the trees the night before.
Day Two, Matt shot a bull out of a herd of ten bulls. It was lounging on sunny Wednesday aftennoon in a place that looked less nasty on the satellite maps than it did when climbing around in there. I suspect the bull and his bachelor group had been undisturbed since opening weekend, having found a place that hunters didn't want to go. The bulls were up and feeding when spotted at noon, a sign of elk that haven't been pushed too hard. Matt and Marcus got back to our camp at 8:30 that night, smiling and completely spent. Llamas to the rescue the following day.
On that Day Three retrieval I shot an elk over two miles from where Matt's bull was hanging, giving the llamas two elk to haul out that day. Again, this group of eight bulls were up and moving at noon. It took 2.5 hours to get above them and in position to shoot the biggest of the five-points in that group. When we got back to camp, we found out Donnie had also shot an elk that day. To retrieve his bull, the llamas would be employed the following morning before we broke camp and headed out the next afternoon.
Point being, at my age and infirmity, there is no way we would shoot four bulls in three days, as far away from roads as we did, if not having access to pack animals. Just not something I am interested in doing (lack of enthusiasm). And as someone mentioned above, in warm weather this location could present serious issues with meat spoilage.
There were a lot of other hunters around the periphery of this area, though not where the bulls were stacked. I suspect some of them scaled the divide as we did. Like I would have done if not having access to pack animals, I suspect most looked down in there and quickly realized what a backpack extraction would require; many heavy trips to climb out of that basin. Without pack animals, I know I would have turned back at the crest of that divide and hoped for a situation that provided a less intimidating extraction, knowing full well my odds of punching a tag would be less.
I know guys, some on this site, who are absolute beasts and can do those nasty extractions without any hesitation. I admire the hell out of them and shake my head at the level of commitment they have to tagging elk on highly pressured public lands. Their relentless determination, a huge factor in their consistent success, makes them far more the minority than the majority, as evidenced by the scarcity of boot tracks in these elk sanctuary areas.
So, to the question in this thread title, "How many times?" For me, the answer is, "Enough to know better." I'll still hunt these locations so long as my knees allow and so long as Beau continues renting llamas.